MCPBA. Conversion of Cyclic Acetals to Hydroxy Esters by MCPBA Oxidation. MCPBA Oxidation, Cyclic Acetals, Hydroxy Esters.
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1 Printed in the Republic of Korea : MCPBA * ( ) Conversion of Cyclic Acetals to Hydroxy Esters by MCPBA Oxidation Keywords: Jin Yeon Kim*, Hakjune Rhee, and Misoo Kim Department of Chemistry, Seonam University, Namweon, Chunrabuk-Do , Korea Department of Chemistry, Hanyang University, Ansan, Kyunggi-Do , Korea Department of Basic Science, Hankyong University, Ansung, Kyunggi-Do ,Korea (Received June 11, 2002) MCPBA,, MCPBA Oxidation, Cyclic Acetals, Hydroxy Esters Various methods for the conversion of aldehydes to esters have appeared in the literatures over the last thirty years. 1 Grieco reported a one-step oxidative conversion of protected lactols into lactones and proposed oxidation mechanism of which was recently proved by the isolation of peroxy intermediate II. 2,3 Scheme Baeyer-Villiger oxidation of ketones and aldehydes using peracid is one of the frequently employed methods for the synthesis of esters due to its ease and high yield. 4 Several methods for direct oxidation of acetal to ester have been reported. 5-8 However, the Baeyer-Villiger reaction of acyclic acetal or ketal with peracid providing the orthocarbonate is known to be sluggish. 9 Therefore, development of an efficient method for direct oxidation of acetals to esters, especially hydroxyesters would be great value since there are a number of methods for the preparation of acetals from the corresponding aldehydes. 10 Thus, we focused our study on the direct oxidation of acetals using MCPBA. Recently, we reported a simple one-pot procedure for the conversion of aldehydes to methyl esters via dimethyl acetal formation from aldehydes and subsequent oxidation by m-chloroperbenzoic acid (MCPBA) with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). 11 Based on the our recent report using MCPBA, we wish to extend this idea to other cyclic acetals which can be converted to the corresponding hydroxy alkyl esters. Cyclic acetals have wide application in organic synthesis as protecting groups of aldehydes, and they can be used for the preparation of hydroxy alkyl esters which are commercially important product Cyclic acetals were easily prepared by a number of methods from the corresponding aldehydes. 10
2 480 The results of the oxidation of cyclic acetals to hydroxy alkyl esters are summarized in Table 1. The presumed oxidation mechanism is shown below and involves the formation and subsequent fragmentation of a peroxy intermediate IV. be applied to the desymmetrization of prochiral diols. In summary, we have demonstrated an efficient conversion of cyclic acetals to their corresponding hydroxy alkyl esters in good to excellent yields through the oxidation using MCPBA. We are currently investigating the oxidation of unsymmetrical cyclic acetals from aldehydes and the desymmetrization of meso-diol with a chiral Lewis acid or a chiral aldehyde using the same methodology. EXPERIMENTAL SECTION Scheme 2. As we obtained in the conversion of aldehydes to methyl esters, 11 all of cyclic acetals provided the hydroxy alkyl esters in good to excellent yields. From the results of the reaction (Table 1), it suggested that any aldehydes can be converted to the corresponding hydroxy alkyl esters. Besides symmetrical cyclic acetals, unsymmetrical cyclic acetals were also converted to hydroxy alkyl acetals. It is worthy of note that unsymmetrical cyclic acetals afforded only one isomer (entries 9 and 10). The results in Table 1 imply that this methodology can General. All reactions were carried out under an inert atmosphere of argon. Chloroform was freshly distilled from phosphorus pentoxide prior to use. Liquid reagents and solvents used were reagent grade and purified prior to use, if necessary, by methods reported in the literature. Analytical thin layer chromatography was performed on pre-coated Merck silica gel 60 F254 TLC plate. Small and mediumscale purification were performed by flash column chromatography by using Merck mesh silica gel. 1 H NMR and 13 C NMR spectral data were obtained on a Varian Gemini 400 (400 MHz) or Varian 300 (300 MHz) spectrometer. Chemical shifts as given in δ ppm relative to CDCl 3 (δ 77.2, 13 C) or Table 1. The conversion of cyclic acetals to the corresponding hydroxy alkyl esters by MCPBA Entry Cyclic Acetal Hydroxy Ester Yield (%) a 1 C 6 H 5 CH(OCH 2 CH 2 O) (1a) C 6 H 5 COOCH 2 CH 2 OH (2a) 73 2 C 6 H 5 CH(OCHMe) 2 (1b) C 6 H 5 COOCHMeCHMeOH (2b) 75 3 C 6 H 5 CH(OCH 2 CH 2 CH 2 O) (1c) C 6 H 5 COOCH 2 CH 2 CH 2 OH (2c) 82 4 p-me-c 6 H 5 CH(OCH 2 CH 2 O) (1d) p-me-c 6 H 5 COOCH 2 CH 2 OH (2d) 84 5 p-me-c 6 H 5 CH(OCHMe) 2 (1e) p-me-c 6 H 5 COOCHMeCHMeOH (2e) 79 6 p-me-c 6 H 5 CH(OCH 2 CH 2 CH 2 O) (1f) p-me-c 6 H 5 COOCH 2 CH 2 CH 2 OH (2f) 77 7 p-meo-c 6 H 5 CH(OCHMe) 2 (1g) p-meo-c 6 H 5 COOCHMeCHMeOH (2g) 81 8 p-meoc 6 H 5 CH(O(CH 2 ) 3O) (1h) p-meo-c 6 H 5 COO(CH 2 ) 3 OH (2h) 83 9 C 6 H 5 CH(OCH(CH 2 CH 2 CH 3 )CH 2 O) (1I) C 6 H 5 COOCH(CH 2 OH)CH 2 CH 2 CH 3 (2i) p-me-c 6 H 5 CH(OCH(CH 2 CH 2 CH 3 )CH 2 O) (1j) p-mec 6 H 5 COOCH(CH 2 OH)CH 2 CH 2 C H 3 (2j) 64
3 MCPBA!"#$ 481 CHCl 3 (δ 7.26, 1 H) which is present as an impurity in CDCl 3 used. Coupling constants (J) are reported in Hertz (Hz). The J values are reported directly as given by the spectrometer, hence slight differences in the coupling constants (J) may be noticed. Multiplicities are abbreviated as follows: singlet (s), doublet (d), triplet (t), quartet (q), and multiplet (m). The relative areas were determined by electronic integration and reported as number of protons, e.g., 1 H. IR spectra were recorded using a BioRad FT-IR spectrophotometer with internal calibration. Mass spectra were recorded on a Shimadzu GCMS-OP 1000 mass spectrometer. Spectral data of products were compared with those in the Aldrich Library of FT 1 H NMR and FT-IR spectra books, and products were identified. Preparation of cyclic acetals; general procedure: To a solution of 5 mmol aldehyde in dried benzene (15 ml) were added 0.25 g of Amberlyst 15 (wet) ion exchange resin and 20 mmol of trimethyl orthoformate under the argon atmosphere at ambient temperature. The solution was stirred at reflux condition. After being stirred for 3 h, 12 mmol of diol was added and the mixture was heated under reflux condition for 8 h. The cyclic acetal formation was monitored by TLC (EtOAc/n-hexane=1:8, v/v). Preparation of benzaldehyde ethylene acetal (1a): To a solution of 5 mmol benzdehyde in dried benzene (15 ml) were added 0.25 g Amberlyst 15 (wet) ion exchange resin and 2.0 mmol of trimethyl orthoformate under the argon atmosphere at ambient temperature. The solution was stirred at reflux condition. After being stirred for 3 h, 12 mmol 1,2-ethandiol was added and the mixture was heated under reflux condition for 8hr. Benzaldehyde ethylene acetal formation was monitored by TLC (EtOAc /n-hexane=1:8, v/v). Preparation of 2-hydroxyethyl benzoate (2a): To a solution of 5.0 mmol of benzaldehyde ethylene acetal in dried benzene (15 ml) were added BF 3 OEt 2 (0.063 ml, 0.50 mmol) and MCPBA (72 %, 1.20 g, 5.0 mmol) under argon atmosphere at ambient temperature. The reaction mixture was stirred for 3 h and then diluted with ethyl acetate (10 ml). The reaction was quenched with 0.5 N NaOH solution (15 ml) and the organic layer was washed with 0.1 N HCl solution (10 ml). The organic layer was dried over anhydrous sodium sulfate, then the filtrate was concentrated. The corresponding desired 2-hydroxyethyl benzoate were purified by flash column chromatography (EtOAc/ n-hexane=1:8, v/v). Yield 73%. TLC (EtOAc/n-hexane=1:8, v/v), R f = IR (neat) 3426, 1720 cm 1. 1 H NMR (400 MHz, CDCl 3 ) d 8.06 (d, J=7.2 Hz, 2H), 7.57 (t, J=7.6 Hz, 1H), 7.44 (t, J=7.6 Hz, 2H), 4.46 (t, J=6.5 Hz, 2H), 3.96 (t, J=6.5 Hz, 2H), 2.45 (brs, 1H). 13 C NMR (75.5 MHz, CDCl 3 ) d , , , , , 66.29, MS (4.10 ev) m/z (rel intensity) 166 (M +, 1.07), 165 (10.80), 124 (10.43), 123 (78.55), 105 (100.0), 77 (69.28). Preparation of meso-1,2-dimethyl-2-hydroxyethyl benzoate (2b) and 3-hydroxypropyl benzoate (2c): To a solution of 5 mmol of benzaldehyde dimethyl acetal in benzene (15 ml) were added 0.25 g of Amberlyst 15 (wet) ion exchange resin and 12 mmol of meso-2,3-butanediol (or 1,3-propanediol) under the argon atmosphere at reflux temperature. After being stirred for 5 h, a catalytic amount of BF 3 OEt 2 and 5.0 mmol of MCPBA were added to the reaction mixture. The resulting reaction mixture was stirred for 1 h at ambient temperature. The reaction mixture was diluted with ethyl acetate (10 ml) and quenched with 0.5 N NaOH solution (15 ml). The organic layer was washed with 0.1 N HCl solution (10 ml) and dried over anhydrous sodium sulfate. The desired hydroxy alkyl esters were purified by flash column chromatography. meso-1,2- Dimethyl-2-hydroxyethyl benzoate (2b): Yield 75%. TLC (EtOAc/n-hexane=1:8, v/v), R f =0.30. IR 3425, 1719 cm 1. 1 H NMR (300 MHz, CDCl 3 ) δ 7.98 (d, J=6.9 Hz, 2H), 7.51 (t, J=7.4 Hz, 1H), 7.38 (t, J=7.7 Hz, 2H), 5.07 (qd, J=6.4, 3.3 Hz, 1H), 3.96 (qd, J=6.5, 3.3 Hz, 1H), 1.57 (brs, 1H), 1.28 (d, J= 6.6 Hz, 3H), 1.19 (d, J=6.3 Hz, 3H). 13 C NMR (75.5 MHz, CDCl 3 ) δ , , , , , 76.03, 69.64, 17.95, MS (3.49 ev) m/z (rel intensity) 195 (M + +1, 1.05), 194 (M +, 0.83), 139 (16.34), 123 (90.50), 105 (100.0). 3-Hydroxypropyl benzoate (2c): Yield 82%. TLC
4 482 (EtOAc/n-hexane = 1:10, v/v), R f = IR (neat) 3425, 1720 cm H NMR (400 MHz, CDCl 3 ) δ 8.02 (d, J=7.3 Hz, 2H), 7.53 (t, J=7.3 Hz, 1H), 7.41 (t, J=7.5 Hz, 2H), 4.45 (t, J=6.3 Hz, 2H), 3.77 (t, J=6.1 Hz, 2H), 3.15 (brs, 1H), 2.00 (quintet, J= 6.2Hz, 2H). 13 C NMR (75.5 MHz, CDCl 3 ) δ , , , , , 61.79, 58.79, MS (4.10 ev) m/z (rel intensity) 181 (M + +1), 123 (90.50), 105 (100), 77 (83.35). 2-Hydroxyethyl 4'-methylbenzoate (2d): Yield 84%. TLC (EtOAc/n-hexane=1:8, v/v), R f =0.25. IR 3443, 1717 cm 1. 1 H NMR (300 MHz, CDCl 3 ) δ 7.94 (d, J=8.1Hz, 2H), 7.22 (d, J = 8.0Hz, 2H), 4.44 (t, J =6.5 Hz, 2H), 3.94 (t, J=6.5 Hz, 2H), 2.41 (s, 3H), 2.29 (brs, 1H). 13 C NMR (75.5 MHz, CDCl 3 ) δ , , , , , 66.46, 61.40, MS (3.33 ev) m/z (rel intensity) 181 (M + +1, 52.34), 180 (M +, 5.59), 137 (63.92), 119 (100.0). 91 (82.46), 84 (11.94), 77 (6.33). meso-1,2-dimethyl-2-hydroxyethyl 4-methylbenzoate (2e): Yield 79%. TLC (EtOAc/n-hexane=1:8, v/v), R f =0.30. IR 3455, 1714 cm 1. 1 H NMR (300 MHz, CDCl 3 ) δ 7.94 (d, J=8.4 Hz, 2H), 7.24 (d, J=8.1 Hz, 2H), 5.11 (qd, J=6.4, 3.3 Hz, 1H), 4.00 (qd, J=6.5, 3.3 Hz, 1H), 2.40 (s, 3H), 2.10 (brs, 1H), 1.33 (d, J=6.6 Hz, 3H), 1.24 (d, J=6.6 Hz, 3H), 13 C NMR (75.5 MHz, CDCl 3 ) δ , , , , , 74.85, 69.72, 21.68, 18.05, MS (2.95 ev) m/z (rel intensity) 209 (M + +1, 31.19), 180 (M +, 16.26), 161 (28.75), 146 (38.64), 135 (32.32), 119 (65.36), 93 (100.0), 74 (40.17), 62 (77.24). 3-Hydroxypropylyl 4'-methylbenzoate (2f): Yield 77%. TLC (EtOAc/n-hexane=1:8, v/v), R f = IR 3440, 1717 cm 1. 1 H NMR (300 MHz, CDCl 3 ) δ 7.92 (d, J=8.1 Hz, 2H), 7.23 (d, J=8.1 Hz, 2H), 4.47 (t, J=6.0 Hz, 2H), 3.76 (t J=6.0 Hz, 2H), 2.40 (s, 3H), 2.21 (brs, 1H), 2.00 (quintet, J=6.3 Hz, 2H). 13 C NMR (75.5 MHz, CDCl 3 ) δ , , , , , 61.61, 59.11, 31.84, MS (4.18 ev) m/z (rel intensity) 194 (M +, 3.98), 138 (25.50), 137 (95.64), 119 (100.0), 89 (99.04), 77 (46.41), 63 (89.63), 57 (49.02). meso-1,2-dimethyl-2-hydroxyethyl 4'-methoxybenzoate (2g): Yield 81%. TLC (EtOAc/n-hexane=1:8, v/v), R f =0.25. IR 3416, 1709 cm 1. 1 H NMR (300 MHz, CDCl 3 ) δ 8.00 (d, J=9.0 Hz, 2H), 6.92 (d, J=9.0 Hz, 2H), 5.11 (qd, J=6.4, 3.3 Hz, 1H), 4.01 (qd, J=6.5, 3.3 Hz, 1H), 3.87 (s, 3H), 1.63 (brs, 1H), 1.33 (d, J=6.6 Hz, 3H), 1.25 (d, J=6.6 Hz, 3H); 13 C NMR (75.5 MHz, CDCl 3 ) δ , , , , , 74.77, 69.86, 55.47, 18.07, MS (2.96 ev) m/z (rel intensity) 225 (M + +1, 5.25), 224 (M +, 19.93), 181 (18.88), 180 (97.85), 153 (88.03), 152 (64.09), 149 (57.41), 136 (33.27), 110 (44.47), 107 (100.0), 105 (88.55), 85 (59.18), 83 (47.14), 78 (44.41), 64 (80.73), 63 (80.02), 55 (63.78). 3-Hydroxypropylyl 4'-metoxybenzoate (2h): Yield 83%. TLC (EtOAc/n-hexane=1:8, v/v), R f = IR 3438, 1711 cm 1. 1 H NMR (300 MHz, CDCl 3 ) δ 7.99 (d, J=9.0 Hz, 2H), 6.92 (d, J=9.0 Hz, 2H), 4.47 (t, J=6.3 Hz, 2H), 3.86 (s, 3H), 3.76 (t, J=6.0 Hz, 2H), 2.61 (brs, 1H), 2.00 (quintet, J=6.3 Hz, 2H). 13 C NMR (75.5 MHz, CDCl 3 ) δ , , , , , 61.49, 59.18, 55.45, MS (3.36 ev) m/z (rel intensity) 210 (M +, 5.71), 153 (74.63), 152 (33.63), 135 (100.0), 109 (13.66), 92 (39.65), 77 (52.21), 71 (19.16), 57 (33.07). 1-Hydroxymethylbutyl benzoate (2i): Yield 65%. TLC (EtOAc/n-hexane=1:8, v/v), R f =0.30. IR 3459, 1722 cm 1. 1 H NMR (300 MHz, CDCl 3 ) δ 8.05 (d, J =7.2 Hz, 2H), 7.54 (t, J=7.4 Hz, 1H), 7.42 (t, J=7.7 Hz, 2H), 5.17 (m, 1H), 3.80 (m, 2H), 1.73 (m, 2H), 1.47 (m, 2H), 0.94 (t, J=7.2 Hz, 3H). 13 C NMR (75.5 MHz, CDCl 3 ) δ , , , , , 69.78, 69.19, 35.60, 18.70, MS (2.30 ev) m/z (rel intensity) 209 (M + +1, 18.30), 208 (M +, 16.31), 190 (37.71), 178 (55.51), 177 (50.86), 139 (72.35), 118 (41.89), 108 (10.57), 104 (100.0), 86 (72.74), 76 (90.91), 68 (87.74), 67 (30.52), 65 (52.32), 59 (19.04). 1-Hydroxymethylbutyl 4'-methylbenzoate (2j): Yield 64%. TLC (EtOAc/n-hexane=1:8, v/v), R f = IR 3440, 1720 cm 1. 1 H NMR (300 MHz, CDCl 3 ) δ 7.93 (d, J=8.4 Hz, 2H), 7.23 (d, J=8.1Hz, 2H), 5.17 (m,1h), 3.80 (m, 2H), 2.31 (s, 3H), 1.74 (m, 2H), 1.45 (m, 2H), 0.96 (t, J=7.2 Hz, 3H). 13 C NMR (75.5 MHz, CDCl 3 ) δ , , , , , 69.88, 69.08, 35.52, 21.63, 18.62, MS (2.94 ev) m/z (rel intensity) 223 (M + +1, 10.07),
5 MCPBA!"#$ (M +, 5.88), 179 (44.16), 151 (30.59), 150 (61.95), 138 (18.73), 137 (70.29), 135 (100.0), 105 (39.04), 89 (86.00), 77 (63.11), 63 (93.86), 58 (89.26), 57 (75.38), 55 (56.51). REFERENCES 1. Larock, R. C. In Comprehensive Organic Transformations: A Guide to Functional Group Preparations, VCH Publishers, Inc., 1989; p 840 and references therein. 2. Grieco, P. A.; Oguri, T. Yokoyama, Y. Tetrahedron Lett. 1978, Sha, C.; Chiu, R.; Yang, C.; Yao, N.; Tseng, W.; Liao, F.; Wang, S. J. Am. Chem. Soc. 1997, 119, For a recent comprehensive review of Baeyer-Villiger reaction, see; Kroe, G. R. In Organic Reactions, John Wiley, 1993, 43, Angyal, S. J.; James, K. Aust. J. Chem. 1971, 24, (a) Delongchamps, P.; Atlani, P. Can. J. Chem. 1974, 52, (b) Sundraaraman, P.; Walker, E. C.; Djerrassi, C. Tetrahedron Lett. 1978, Hosokawa, T.; Imada, Y.; Murahashi, S.-I. J. Chem. Soc., Chem. Commun. 1983, Chidambaram, N.; Bhat, S.; Changdrasekaran, S. J. Org. Chem. 1992, 57, (a) Bailey, W. F.; Bichoff, J. J. J. Org. Chem. 1985, 50, (b) Bailey, W. F.; Shin, M. J. Am. Chem. Soc. 1982, 104, (c) Gaoni, Y. J. Chem. Soc. (C) 1968, d) Gaoni, Y. J. Chem. Soc. (C) 1968, MacPherson, D. T.; Rami, H. K. In Comprehensive Organic Functional Group Transformations, Kartritzky, A. R.; Otto, M. Rees, C. W. Eds., Elsevier Science Ltd., 1995; Vol. 4, p Rhee, H.; Kim, J. Y. Tetrahedron Lett. 1998, 39, Curini, M.; Epifano, F.; Marcotullio, M. C.; Rosati, O. Synlett 1999, Nai-ju, H.; Liang-heng, X. Synth. Commun. 1990, 20, Murahashi, S. I.; Oda, Y.; Naota, T. Chem. Lett. 1992, Prugh, J. D.; McCarty, W. C. Tetrahedron Lett. 1966, Bhat, S.; Ramesha, A. R. Synlett 1995, 329.
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