Masatoshi Shibuya,Takahisa Sato, Masaki Tomizawa, and Yoshiharu Iwabuchi* Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences,
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1 Oxoammonium ion/naclo 2 : An Expedient, Catalytic System for One-pot Oxidation of Primary Alcohols to Carboxylic Acid with Broad Substrate Applicability Masatoshi Shibuya,Takahisa Sato, Masaki Tomizawa, and Yoshiharu Iwabuchi* Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, Aobayama 6-3, Sendai , Japan. Supporting Information Table of Contents: General Experimental Procedures S2 Procedure for Preparation of Oxoammonium salts S3 Procedure for Oxidation of Primary alcohols to Carboxylic Acids S3 Experimental Data for Compounds S6 1 H and 13 C Spectra S9
2 General Experimental Procedures: Yields refer to chromatographically and spectroscopically ( 1 H NMR) homogeneous materials unless otherwise stated. Reagents were purchased from commercial sources and used without further purification unless otherwise stated. Reactions were monitored by thin-layer chromatography (TLC) carried out on 0.25 mm silica gel plates (60 F 254 ) using UV light as visualizing agent and p-anisaldehyde in ethanol/aqueous H 2 SO 4 /CH 3 CO 2 H for staining. Column chromatography was performed using silica gel 60 particle size µm. Chemical shift (δ) is reported in parts per million (ppm) downfield relative to tetramethylsilane (TMS) or CDCl3 (77.10 ppm). Coupling constants (J) are reported in Hz. Multiplicities are reported using the following abbreviations: s, singlet; d. doublet; t, triplet; q, quartet; m, multiplet; br, broad; app, Apparent.
3 General Procedure for Preparation of Oxoammonium Salts : Synthesis of Me-AZADO + Cl - Cl 2 gass was bubbled to the mixture of Me-AZADO (500 mg, 3.01 mmol) and CCl 4 (6 ml) at RT. After stirring for 30 min, the red precipitate was filtered and washed with Et 2 O and dried in vacuo to yield Me-AZADO+Cl- (560 mg, 2.78 mmol, 92%): Anal: Calcd. for C 10 H 16 ClNO: C, 59.61; H, 8.02; N, 6.94 found: C,59.55; H, 8.00; N, IR (neat, cm -1 ): 2934, MS m/z 166 (M -Cl), 93 (100%); HRMS Calcd. C 10 H 16 NO: , found: Synthesis of Me-AZADO + BF 4 Me-AZADO (1.0 g, 6.6 mmol) was slurried with H 2 O (6 ml) and 42% HSbF 6 (1.4 ml, 6.6 mmol) was slowly added dropwise over 30 min at room temperature. After the solution turned to amber color, NaOCl (1.5 ml, 3.0 mmol) was added over 1 h at 0 o C and stirred for additional 1 h at 0 o C. The reaction mixture was filtered and the yellow crystalline precipitate was washed with ice-cold 5% NaHCO 3 (10 ml), water (10 ml) and ice-cold Et 2 O (50 ml). The solid was dried over 24 h at 50 o C in vacuo to yield Me-AZADO + - BF 4 (1.1 g, 4.53 mmol, 75 %) as the bright yellow solid: Anal: Calcd. for C 10 H 16 BF 4 NO: C, 47.46; H, 6.37; N, 5.54 found: C,47.34; H, 6.37; N, IR (neat, cm -1 ): 2940, 1617 Procedure for Oxidation of Primary alcohols to Carboxylic Acids Representative procedure To a stirring mixture of primary alcohol (1 mmol) in sodium phosphate buffer (1.0 M, ph 6.8, 0.3 M) and MeCN (0.3 M), NaClO2 (80%) (3 mmol) and 1-Me-AZADO (0.05 mmol) was added. After completion of the reaction (monitored by TLC), 2-methyl-2-butene (1 ml) was added. H 2 O was poured to the mixture and the mixure was extracted with AcOEt. The
4 aqueous layer was adjusted to ph with 10% HCl and extracted with AcOEt twice. The combined organic layer was washed with acidic brine and then concentrated to give the crude carboxylic acid. The crude carboxylic acid was diluted by Et 2 O or CH 2 Cl 2 and treated with CH2N2, followed by removal of excess CH 2 N 2 and solvent. Purification by column chromatography provided methyl ester. Procedure for oxidation on large scale oxidation 5 g of cinnamyl alcohol To a stirring mixure of cinnamyl alcohol (4) (5 g, 37 mmol) and 1-Me-AZADO + Cl - (372 mg, 1.85 mmol) in MeCN (62 ml) and sodium phosphate buffer (1.0 M, ph 6.8, 62 ml), NaClO 2 (80%)(12.5 g, 165 mmol) was slowly added over 15 min.after stirring for 8 h at 40 o C, 2-methyl-2-butene (4 mol) was added. H 2 O (10 ml) was added and the mixure was extracted with AcOEt and was further purified with extraction using 5% NaOH. The aqueous layer was acidified with 10% HCl to afford colorless precipitate of cinnamic acid. The precipitate was collected on a filter and washed with H 2 O. and dried in vacuo to afford cinnamic acid (4.76 g, 32.2 mmol, 87%) as a colorless powder: 1 H-NMR (400MHz, ) δ 7.80 (2H, d, J = 15.5 Hz), (2H, m), (3H, m), 6.46 (2H, d, J = 15.5 Hz). 13 C-NMR (100MHz, ) δ 172.7, 147.1, 134.0, 130.7, 128.9, 128.3, IR (neat, cm -1 ): 3023, 1681, 1630, 1313, MS m/z 148 (M ), 147 (100%); HRMS Calcd. C 9 H 8 O 2 : , found: g of 2-(3,4-dimethoxyphneyl)ethanol To a stirring mixure of 2-(3,4-dimethoxyphenyl)ethanol (6) (10 g, 55 mmol) and 1-Me-AZADO + Cl - (550 mg, 2.7 mmol) in MeCN (90 ml) and sodium phosphate buffer (1.0 M, ph 6.8, 90 ml), NaClO 2 (80%)(18.6 g, 165 mmol) was slowly added over 20 min.after stirring for 2 h at 25 o C, 2-methyl-2-butene (5 mol) was added. H 2 O (10 ml) was added and
5 the mixure was extracted with AcOEt and was further purified with extraction using 5% NaOH. The aqueous layer was washed with Et 2 O and acidified with 10% HCl and then extracted with AcOEt. The organic layer was evaporated and the crude products was recrystalization from AcOEt-hexane to afford 3,4-dimethoxyphenyl acetic acid (9.26 g, 47.2 mmol) as a colorless prism: 1 H-NMR (400MHz, ) δ 6.82 (2H, s), 6.80 (1H, s), 3.87 (3H, s), 3.86 (3H, s), 3.59 (3H, s). 13 C-NMR (100MHz, ) δ 178.1, 148.9, 148.2, 125.6, 121.5, 112.4, 111.1, 55.7, 55.7, IR (neat, cm -1 ): 3501, 2938, 1711, 1515, MS m/z 196 (M ), 151 (100%); HRMS Calcd. C 10 H 12 O 4 : , found:
6 Experimental Data for Compounds: Methyl 2-(3,4-Dimethoxyphenyl)acetate (6b) 1 H-NMR (400MHz, ) δ (3H, s), 3.87 (3H, s), 3.86 (3H, s), 3.69 (3H, s), 3.56 (2H, s). 13 C-NMR (100MHz, ) δ 172.0, 148.7, 148.0, 126.3, 121.2, 112.3, 111.1, 55.6, 55.6, 51.7, IR (neat, cm -1 ): 2952, MS m/z 210 (M ), 151 (100%); HRMS Calcd. C 11 H 14 O 4 : , found: (1-Phenylcyclohexyl)methanol (8a) mp o C (recrystallized from hexane in a freezer). 1 H-NMR (400MHz, ) δ (4H, m), (1H, m), 3.49 (2H, s), 2.15 (2H, d, J = 8.9 Hz), (8H, m). 13 C-NMR (100MHz, ) δ 143.8, 128.6, 127.3, 126.1, 73.0, 43.9, 32.5, 26.6, IR (neat, cm -1 ): 3389, MS m/z 190 (M ), 159 (100%); HRMS Calcd. C 13 H 18 O: , found: Methyl 1-phenylcyclohexancarboxylate (8b) 1 H-NMR (400MHz, ) δ 7.37 (2H, d, J = 7.6 Hz), 7.29 (2H, m), 7.19 (1H, t, J = 7.2 Hz), 3.60 (3H, s), 2.48 (2H, d, J = 12.4 Hz ), (5H, m), (2H, m), (1H, m). 13 C-NMR (100MHz, ) δ 175.4, 143.7, 128.2, 126.5, 125.7, 51.8, 50.8, 34.7, 25.5, IR (neat, cm -1 ): 2936, MS m/z 218 (M ), 159 (100%); HRMS Calcd. C 14 H 18 O 2 : , found: Methyl 2,4,6-trimethylbenzoate (9b) 1 H-NMR (400MHz, ) δ 6.85 (2H, s), 3.89 (3H, s), 2.28 (9H, s). 13 C-NMR (100MHz, ) δ 170.5, 139.2, 135.1, 130.8, 128.3, 51.6, 21.0, IR (neat, cm -1 ): 2951, MS m/z 178 (M ), 147 (100%); HRMS Calcd. C 11 H 14 O 2 : , found:
7 Methyl 3-phenylpropinolate (10b) 1 H-NMR (400MHz, ) δ 7.58 (2H, d, J = 7.8 Hz), 7.45 (1H, t, J = 7.8 Hz), 7.37 (2H, t, J = 7.8 Hz), 3.84 (3H, s). 13 C-NMR (100MHz, ) δ 154.3, 132.8, 130.5, 128.4, 119.4, 86.3, 80.3, IR (neat, cm -1 ): 3403, 2953, 2226, 1714, 1289, 1203, MS m/z 160 (M ), 129 (100%); HRMS Calcd. C 10 H 8 O 2 : , found: Hydroxy 2-methylheptanol (11a) 1 H-NMR (400MHz, ) δ 3.47 (1H, dd, J = 10.7, 5.3 Hz), 3.41 (1H, dd, J = 10.7, 5.4 Hz), (10H, m), 1.17 (3H, s), 0.89 (3H, t, J = 6.8 Hz). 13 C-NMR (100MHz, ) δ 73.1, 69.6, 38.6, 32.4, 23.4, 23.0, 22.5, IR (neat, cm -1 ): 3389, MS m/z 131 (M -Me), 115 (100%); HRMS Calcd. C 7 H 15 O 2 : , found: Methyl 2-hydroxy 2-methylheptanoate (11b) 1 H-NMR (400MHz, ) δ 3.78 (3H, s), 3.12 (1H, s), (2H, m), (5H, m), 1.40 (3H, m), (1H, m), 0.87 (3H, t, J = 6.9 Hz). 13 C-NMR (100MHz, ) δ 177.6, 74.6, 52.5, 40.1, 31.7, 25.9, 23.2, 22.3, IR (neat, cm -1 ): 3526, 2955, FAB-MS m/z 175 (M +H) ; HRMS Calcd. C 9 H 19 O 3 : , found: Prenyloxypentanol (13a) 1 H-NMR (400MHz, ) δ 5.35 (1H, dd, J = 6.9, 5.5 Hz), 3.94 (2H, d, J = 6.9 Hz), 3.64 (2H, t, J = 6.4 Hz), 3.42 (2H, t, J = 6.5 Hz), 1.74 (3H, s), 1.67 (3H, s), (m, 5H), (m, 2H). 13 C-NMR (100MHz, ) δ 136.4, 121.0, 69.8, 67.0, 62.0, 32.2, 29.2, 25.5, 22.2, IR (neat, cm -1 ): 3390, MS m/z 172 (M ), 69 (100%); HRMS Calcd. C 10 H 20 O 2 (M + ): , found: Methyl 5-prenyloxypentanoate (13b) 1 H-NMR (400MHz, ) δ 5.34 (1H, t, J = 6.9 Hz), 3.93 (2H, d, J = 6.9 Hz), 3.66 (3H, s), 3.41 (2H, t, J = 6.3 Hz), 2.34 (2H, t, J = 7.4 Hz), 1.74 (3H, s), (4H, m), 1.67
8 (3H, s). 13 C-NMR (100MHz, ) δ 173.9, 136.6, 121.1, 69.5, 67.2, 51.3, 33.7, 29.1, 25.7, 21.7, IR (neat, cm -1 ): 2934, MS m/z 200 (M ), 115 (100%); HRMS Calcd. C 11 H 20 O 3 (M + ): , found: Tetrahydroabietyl alcohol (14a) IR (neat, cm -1 ): 3391, MS m/z 292 (M ), 261 (100%); HRMS Calcd. C 20 H 36 O: , found: Methyl tetrahydroabietate (14b) IR (neat, cm -1 ): 2926, MS m/z 320 (M ), 163 (100%); HRMS Calcd. C 21 H 36 O 2 (M + ): , found: tert-butyl 5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxa-5-ylcalbamate (17a) 1 H-NMR (400MHz, ) δ 5.32, (1H, br-s), 4.23 (1H, br-s), 3.85 (2H, d, J = 11.5 Hz), 3.54 (2H, d, J = 11.5 Hz), 3.73 (2H, d, J = 6.5 Hz), 1.45 (12H, s), 1.44 (3H, s). 13 C-NMR (100MHz, ) δ 156.3, 98.7, 80.4, 64.6, 64.2, 53.3, IR (neat, cm -1 ): 3303, 2978, FAB-MS m/z 262 (M ), 148 (100%); HRMS Calcd. C 12 H 24 NO 5 : , found: Methyl tert-butyl 5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxa-5-carboxylate (17b) 1 H-NMR (400MHz, ) δ 5.45, (1H, br-s), 4.20 (2H, d, J = 11.7 Hz), 3.91 (2H, d, J = 11.7 Hz), 3.76 (3H, s), 1.47, (3H, s), 1.44 (12H, s). 13 C-NMR (100MHz, ) δ 170.4,154.7, 98.7, 80.3, 64.1, 56.1, 52.4, 28.0, IR (neat, cm -1 ): 3340, 2991, 1747, FAB-MS m/z 290 (M ), 176 (100%); HRMS Calcd. C 13 H 24 NO 6 : , found:
9 (400 MHz) MeO CO 2 Me 6.15 MeO
10 MeO CO 2 Me MeO (100 MHz) Supplementary Material (ESI) for Chemical Communications
11 (400 MHz) OH 9.96 Ph
12 Ph OH (100 MHz) Supplementary Material (ESI) for Chemical Communications
13 (400 MHz) CO 2 Me Ph
14 Ph CO 2 Me (100 MHz) Supplementary Material (ESI) for Chemical Communications
15 (400 MHz) CO 2 Me 9.40
16 CO 2 Me (100 MHz) Supplementary Material (ESI) for Chemical Communications
17 (400 MHz) Ph CO 2 Me
18 Ph CO 2 Me (100 MHz) Supplementary Material (ESI) for Chemical Communications
19 (400 MHz) HO OH 6.06
20 HO OH (100 MHz) Supplementary Material (ESI) for Chemical Communications
21 (400 MHz) HO CO 2 Me 11.11
22 (400 MHz) HO CO 2 Me
23 (400 MHz) OH O 11.11
24 (100 MHz) OH O
25 (400 MHz) using Me-AZADO + Cl - CO 2 Me O 12.46
26 (400 MHz) using Me-AZADO + - BF 4 CO 2 Me O 11.24
27 (100 MHz) CO 2 Me O
28 (400 MHz) BocHN OH O O 16.35
29 O O BocHN OH (100 MHz) Supplementary Material (ESI) for Chemical Communications
30 (400 MHz) BocHN CO 2 Me O O 15.96
31 (100 MHz) BocHN CO 2 Me O O
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