European Journal of Organic Chemistry
10.1002/ejoc.201601144
FULL PAPER
66.6, 66.5, 39.7, 39.2 ppm. HRMS (ESI): m/z calcd. for C10H13BrNa 48.7, 48.5, 41.9, 27.2, 27.1, 23.3, 22.8, 19.3, 19.2, 18.1, 18.0 ppm. MS
[M+Na]+ 282.9940; found 282.9937.
(ESI) m/z 221 (M-H-, 100%).
2-Methyl-4-phenylbutane-1,2,4-triol
(2i).[33]
55:45
mixture
of 3-(1-Hydroxycyclohexyl)propane-1,2-diol (2p).[35] 1:1 mixture of
diasteromers; Colorless oil; 95% yield; 1H NMR (CDCl3): δ 7.29-7.18 (5H, diasteromers; Colorless solid; 71% yield; 1H NMR (CDCl3): δ 4.45 (1H, br
m, ArH), 5.15-4.75 (2H, m, OH and OCHPh), 3.67 (1H, d, J = 11.3 Hz, s, OH), 4.06 (1H, ddd, J = 9.3 and 6.9 and 3.6 Hz, OCH), 3.56 (1H, dd, J =
CHHO), 3.47 (1H, d, J = 11.3 Hz, OCHH), 3.36 (2H, br s, 2 x OH), 2.08- 11.6 and 3.3 Hz, OCHH), 3.46 (2H, br s, 2 x OH), 3.42 (1H, dd, J = 11.6
1.96 (0.45H, m, CHH), 1.94-1.75 (0.55H, m, CHH), 1.76-1.64 (0.55H, m, and 6.6 Hz, OCHH), 1.77-1.17 (12H, m, 6 x CH2) ppm. 13C NMR (CDCl3): δ
CHH), 1.64-1.46 (0.45H, m, CHH), 1.20 (1.35H, s, CH3), 1.13 (1.65H, s, 72.2, 69.2, 67.1, 42.0, 39.7, 36.0, 25.7, 22.2, 22.0 ppm. MS (ESI) m/z 197
CH3) ppm. 13C NMR (CDCl3): δ 144.3, 144.1, 128.4, 127.5, 127.4, 125.7, (M+Na+, 100%).
125.6, 73.6, 73.4, 71.5, 71.0, 70.2, 68.7, 46.8, 46.0, 25.0, 23.5 ppm. MS
(ESI) m/z 195 (M-H-, 100%).
3-(2,3-Dihydroxypropyl)-3-hydroxy-1-methylindolin-2-one (2q). 1:1
mixture of diasteromers; Orange oil; 50% yield; 1H NMR (CDCl3): δ 7.49-
3-Methyl-4-phenylbutane-1,2,4-triol (2j). 1:1:1:1 mixture of diasteromers; 7.38 (1H, m, ArH), 7.37-7.18 (1H, m, ArH), 7.13-6.96 (1H, m, ArH), 6.85-
Viscous colorless oil; 87% yield; 1H NMR (CDCl3): δ 7.32-7.10 (5H, m, 6.71 (1H, m, ArH), 5.07 (1H, br s, OH), 4.51-4.30 (1H, m, OCH), 4.17 (1H,
ArH), 5.08 (0.5H, d, J = 2.1 Hz, OCHPh), 4.98 (0.5H, d, J = 2.5 Hz, br s, OH), 3.70-3.39 (3H, m, OH and OCH2), 3.15 (1.5H, s, NCH3), 3.12
OCHPh), 4.82 (2H, br s, OH), 4.54-4.44 (1H, m, OCH), 4.16-4.02 (0.25H, (1.5H, s, NCH3), 2.46-2.23 (1H, m CHH), 2.21-1.96 (1H, m, CHH) ppm. 13
C
m, OCHH), 3.95-3.85 (0.25H, m, OCHH), 3.77-3.42 (2.5H, m, OCH2 and NMR (CDCl3): δ 178.7, 178.5, 142.6, 142.3, 130.7, 129.7, 124.3, 123.6,
OH), 1.98-1.76 (1H, m, CHCH3), 0.69 (0.75H, d, J = 7.1 Hz, CH3), 0.60 123.5, 108.8, 108.7, 75.8, 75.7, 68.6, 68.3, 66.3, 66.2, 39.8, 39.2, 26.3,
(0.75H, d, J = 7.0 Hz, CH3), 0.52 (0.75H, d, J = 7.0 Hz, CH3), 0.44 (0.75H, 26.2 ppm. HRMS (ESI): m/z calcd. for C12H14NO4 [M-H]- 236.0928; found
d, J = 6.9 Hz, CH3) ppm. 13C NMR (CDCl3): δ 142.8, 142.7, 142,4, 142.2, 236.0922.
128.4, 128.1, 128.0, 127.8, 127.7, 127.1, 127.0, 126.9, 126.8, 125.9,
125.7, 78.6, 76.7, 76.2, 75.8, 75.7, 74.2, 73.6, 72.4, 65.0, 64.9, 64.6, 64.4,
41.8, 41.6, 41.5, 41.4, 12.7, 10.9, 9.7 ppm. HRMS (ESI): m/z calcd. for
C11H16NaO3 [M+Na]+ 219.0992; found 219.1001.
N-(3,4-Dihydroxy-1-phenylbutyl)methanesulfonamide
(2r).
55:45
mixture of diasteromers; Colorless oil; 74% yield; 1H NMR (CDCl3): δ 7.40-
7.17 (5H, m, ArH), 6.57 (0.45H, d, J = 6.4 Hz, NH), 6.51 (0.55H, d, J = 8.8
Hz, NH), 4.83-4.55 (1H, m, NCHPh), 4.36-3.93 (2H, m, OH and OCH),
of 3.80-3.37 (3H, m, OH and OCH2), 2.55 (1.65H, s, CH3), 2.45 (1.35H, s,
3,3-Dimethyl-4-phenylbutane-1,2,4-triol
(2k).
1:1
mixture
diasteromers; White solid; 82% yield; 1H NMR (CDCl3): δ 7.27-7.21 (5H, m, CH3), 2.15-1.63 (2H, m, CH2) ppm. 13C NMR (CDCl3): δ 141.7, 141.2,
ArH), 5.15-5.12 (2H, br s, 2 x OH), 4.63 (1H, s, OCHPh), 3.75-3.42 (4H, m, 128.9, 128.0, 127.7, 126.9, 126.4, 70.2, 68.7, 66.5, 66.3, 56.7, 54.8, 41.6,
OH, OCH and OCH2), 0.84 (1.5H, s, CH3), 0.76 (3H, s, CH3), 0.58 (1.5H, s, 41.5, 40.1, 40.0 ppm. HRMS (ESI): m/z calcd. for C11H16NO4S [M-H]-
CH3) ppm. 13C NMR (CDCl3): δ 140.6, 128.1, 127.9, 127.5, 127.4, 127.4, 258.0806; found 258.0805.
80.4, 80.2, 79.8, 77.6, 63.1, 62.7, 40.7, 39.8, 22.5, 21.1, 19.8, 15.0 ppm.
HRMS (ESI): m/z calcd. for C12H17O3 [M-H]- 209.1183; found 209.1183.
2,3-Dihydroxypropyl benzoate (2s).[36] Υellow oil. 51% yield; 1H NMR
(CDCl3): δ 8.01 (2H, d, J = 7.0 Hz, ArH), 7.60-7.48 (1H, m, ArH), 7.46-7.33
6-Phenylhexane-1,2,4-triol (2l).[34] 1:1 mixture of diasteromers; Yellow oil; (2H, m, ArH), 4.39 (2H, d, J = 5.4 Hz, OCH2), 4.14-3.99 (1H, m, OH), 3.97-
70% yield; 1H NMR (CDCl3): δ 7.32-7.10 (5H, m, ArH), 4.12-3.35 (7H, m, 3 3.90 (1H, m, OCH), 3.82-3.50 (4H, m, 2 x OH and OCH2) ppm. 13C NMR
x OH and 2 x OCH and OCH2), 2.86-2.49 (2H, m, CH2Ph), 1.85-1.68 (2H, (CDCl3): δ 167.7, 133.3, 129.7, 129.5, 128.4, 70.3, 65.6, 63.4 ppm. MS
m, CH2), 1.66-1.43 (2H, m, CH2) ppm. 13C NMR (CDCl3): δ 141.9, 141.7, (ESI) m/z 219 (M+Na+, 100%).
128.3, 128.3, 125.8, 122.3, 72.3, 70.9, 69.2, 67.7, 66.8, 66.5, 39.5, 39.4,
39.0, 38.9, 32.0, 31.6 ppm. MS (ESI) m/z 209 (M-H-, 100%).
1-Phenylethane-1,2-diol (3a).[18] Colorless oil; 98% yield; 1H NMR
(CDCl3): δ 7.25 (5H, m, ArH), 4.75 (1H, dd, J = 7.8 and 3.9 Hz, OCHPh),
Decane-1,2,4-triol (2m).[32] 1:1 mixture of diasteromers; Viscous orange 4.19 (2H, br s, 2 x OH), 3.70-3.51 (2H, m, OCH2) ppm. 13C NMR (CDCl3): δ
1
oil; 89% yield; H NMR (CDCl3): δ 4.65-4.32 (3H, br s, 3 x OH), 3.98-3.67 140.0, 128.4, 127.9, 126.0, 74.7, 67.8 ppm. MS (ESI) m/z 137 (M-H-,
(2H, m, 2 x OCH), 3.59-3.25 (2H, m, OCH2), 1.57-1.12 (12H, m 6 x CH2), 100%).
0.91-0.74 (3H, m, CH3) ppm. 13C NMR (CDCl3): δ 72.4, 71.6, 69.2, 68.2,
1-(4-Chlorophenyl)ethane-1,2-diol (3b).[37] Colorless oil; 41% yield; 1H
NMR (CDCl3): δ 7.36-7.17 (4H, m, ArH), 5.15-4.52 (3H, m, 2 x OH and
66.9, 66.5, 39.5, 39.0, 38.0, 37.8, 31.8, 29.3, 25.8, 25.4, 22.6, 14.0 ppm.
MS (ESI) m/z 189 (M-H-, 100%).
PhCH), 3.79-3.42 (2H, m, CH2) ppm. 13C NMR (CDCl3): δ 138.8, 133.6,
4-Cyclohexylbutane-1,2,4-triol (2n).[16] 1:1 mixture of diasteromers; 128.6, 127.5, 73.9, 67.6 ppm. MS (ESI) m/z 171 (M-H-, 100%).
Viscous white oil; 80% yield; 1H NMR (CDCl3): δ 4.07-3.87 (1H, m, OCH),
1-(4-(tert-Butyl)phenyl)ethane-1,2-diol (3c).[38] White solid; 86% yield; 1H
NMR (CDCl3): δ 7.36 (2H, d, J = 8.4 Hz, ArH), 7.25 (2H, d, J = 8.4 Hz,
3.73-3.42 (3H, m, 1 x OCH and OCH2), 2.73 (3H, br s, 3 x OH), 1.92-1.52
(5H, m, 1 x CH and 2 x CH2), 0.42-0.83 (8H, m, 4 x CH2) ppm. 13C NMR
(CDCl3): δ 76.0, 72.7, 72.2, 69.4, 67.0, 66.6, 44.1, 43.9, 36.4, 35.8, 29.0,
28.8, 28.2, 28.0, 26.4, 26.2, 26.1 ppm. MS (ESI) m/z 187 (M-H-, 100%).
ArH), 4.85-4.66 (1H, m, PhCH), 3.92-3.40 (4H, m, CH2 and 2 x OH), 1.30
[9H, s, C(CH3)3] ppm. 13C NMR (CDCl3): δ 150.8, 137.5, 125.8, 125.4,
74.9, 67.9, 34.5, 31.3 ppm. MS (ESI) m/z 193 (M-H-, 100%).
3-(Hydroxy(phenyl)methyl)cyclohexane-1,2-diol (2o).[16] 50:25:20:5
mixture of diastereomers; Colorless oil; 91% yield; 1H NMR (CDCl3): δ
7.31-7.12 (5H, m, ArH), 5.83 (2H, br s, 2 x OH), 5.10 (0.25H, d, J = 0.7 Hz,
OCHPh), 4.96 (0.5H, d, J = 2.6 Hz, OCHPh), 4.76 (0.2H, d, J = 9.9 Hz,
OCHPh), 4.52 (0.05H, d, J = 8.8 Hz, OCHPh), 3.98-3.76 (1H, m, OCH),
3.62-3-31 (1H, m, OCH), 2.24-0.90 (7H, m, OH and 3 x CH2) ppm. 13C
NMR (CDCl3): δ 142.8, 142.5, 142.4, 128.4, 128.1, 128.0, 127.1, 127.0,
126.9, 126.0, 125.8, 77.5, 77.4, 75.8, 75.8, 75.7, 75.5, 74.3, 72.7, 70.0,
1-(p-Tolyl)ethane-1,2-diol (3d).[37] White solid; 88% yield; 1H NMR
(CDCl3): δ 7.19 (2H, d, J = 8.2 Hz, ArH), 7.11 (2H, d, J = 8.2 Hz, ArH),
4.72 (1H, dd, J = 7.8 and 3.9 Hz, PhCH), 3.68 (2H, br s, 2 x OH), 3.69-3.52
(2H, m, CH2), 2.32 (3H, s, CH3) ppm. 13C NMR (CDCl3): δ 137.5, 137.3,
129.1,126.0, 74.5, 67.9, 21.1 ppm. MS (ESI) m/z 151 (M-H-, 100%).
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