General Papers ARKIVOC 2009 (ii) 68-75
200.3 ppm. Anal. Calcd for C15H16O2S: C, 69.23; H, 6.15; S, 12.30; found: C, 69.25; H, 6.17; S, 12.32. 3-Hydroxy-2-methyl-3-(4-(methylthio)phenyl)-1-phenylpropan-1-one (3bc). A colorless oil, IR (neat): . (cm-1): 3450, 3070, 2925, 1674, 1595, 1488. Data for major isomer. 1H NMR (500 MHz, CDCl3, 25°C): d = 1.24 (d, J = 7.2 Hz, 3H), 2.53 (s, 3H), 3.64 (d, J = 4.5 Hz, OH), 3.73 (m, 1H), 5.25 (m, 1H), 7.29 (m, 2H), 7.36 (m, 2H), 7.51 (m, 2H), 7.61 (m, 1H), 7.99 (d, J = 7.8 Hz, 2H) ppm. 13C NMR (125 MHz, CDCl3, 25°C): d = 12.8, 28.7, 47.9, 53.8, 127.8, 128.1, 128.6, 128.8, 129.8, 139.5, 139.7, 140.4, 201.6 ppm. Data for minor isomer. 1H NMR (500 MHz, CDCl3, 25°C): d = 1.13 (d, J = 7.2 Hz, 3H), 2.53 (s, 3H), 2.99 (d, J = 3.4 Hz, OH), 3.86 (m, 1H), 5.02 (m, 1H), 7.29 (m, 2H), 7.39 (m, 2H), 7.53 (m, 2H), 7.65 (m, 1H), 8.02 (d, J = 7.5 Hz, 2H) ppm. 13C NMR (125 MHz, CDCl3, 25°C): d = 12.4, 26.7, 45.8, 51.8, 127.3, 127.5, 128.4, 128.9, 129.5, 137.5, 139.8, 141.2, 201.5 ppm. Anal. Calcd for C17H18O2S: C, 71.32; H, 6.29; S, 11.18; found: C, 71.35; H, 6.31; S, 11.17. 3-Hydroxy-2-methyl-3-(5-methylthiophen-2-yl)-1-phenylpropan-1-one (3cc). A yellowish oil, IR (neat): . (cm-1): 3487, 3070, 2925, 1676, 1595, 1450. Data for major isomer. 1H NMR (500 MHz, CDCl3, 25°C): d = 1.21 (d, J = 7.2 Hz, 3H), 2.50 (s, 3H), 3.18 (d, J = 5.0 Hz, OH), 3.91 (m, 1H), 5.21 (m, 1H), 6.64 (m, 1H), 6.86 (d, J = 3.5 Hz, 1H), 7.51 (m, 2H), 7.62 (m, 1H), 8.05 (d, J = 7.4 Hz, 2H) ppm. 13C NMR (125 MHz, CDCl3, 25°C): d = 15.9, 45.1, 59.6, 71.2, 110.4, 124.6, 127.8, 129.1, 129.7, 133.7, 136.9, 154.5, 202.2 ppm. Data for minor isomer. 1H NMR (500 MHz, CDCl3, 25°C): d = 1.38 (d, J = 7.2 Hz, 3H), 2.49 (s, 3H), 3.41 (d, J = 2.7 Hz, OH), 3.87 (m, 1H), 5.41 (m, 1H), 6.64 (m, 1H), 6.82 (d, J = 3.5 Hz, 1H), 7.55 (m, 2H), 7.64 (m, 1H), 7.99 (d, J = 7.7 Hz, 2H) ppm. 13C NMR (125 MHz, CDCl3, 25°C): d = 11.9, 44.6, 49.1, 68.6, 108.5, 123.7, 127.2, 128.9, 129.5, 133.1, 135.4, 151.6, 201.2 ppm. Anal. Calcd for C15H16O2S: C, 69.23; H, 6.15; S, 12.30; found: C, 69.25; H, 6.17; S, 12.32. 3-Hydroxy-2-methyl-3-(5-bromothiophen-2-yl)-1-phenylpropan-1-one (3dc). A yellowish oil, IR (neat): . (cm-1): 3452, 3070, 2927, 1674, 1595, 1448. Data for major isomer. 1H NMR (500 MHz, CDCl3, 25°C): d = 1.26 (d, J = 7.2 Hz, 3H), 3.48 (d, J = 5.6 Hz, OH), 3.89 (m, 1H), 5.21 (m, 1H), 6.81 (d, J = 3.7 Hz, 1H), 6.94 (d, J = 3.7 Hz, 1H), 7.56 (m, 2H), 7.67 (m, 1H), 8.02 (d, J = 7.5 Hz, 2H) ppm. 13C NMR (125 MHz, CDCl3, 25°C): d =16.2, 48.1, 67.5, 112.4, 125.4, 128.9, 129.3, 129.9, 134.2, 136.6, 148.5, 205.2 ppm. Data for minor isomer. 1H NMR (500 MHz, CDCl3, 25°C): d = 1.36 (d, J = 7.2 Hz, 3H), 3.67 (d, J = 2.5 Hz, OH), 3.79 (m, 1H), 5.43 (m, 1H), 6.78 (d, J = 3.7 Hz, 1H), 6.96 (d, J = 3.7 Hz, 1H), 7.52 (m, 2H), 7.63 (m, 1H), 7.99 (d, J = 7.8 Hz, 2H) ppm. 13C NMR (125 MHz, CDCl3, 25°C): d = 12.5, 53.8, 70.9, 111.5, 124.1, 128.9, 129.2, 129.8, 134.0, 135.8, 147.9, 204.8 ppm. Anal. Calcd for C14H13O2SBr: C, 51.69; H, 4.00; S, 9.84; found: C, 51.70; H, 3.98; S, 9.85. 3-Hydroxy-2-methyl-3-(3-methylthiophen-2-yl)-1-phenylpropan-1-one (3ec). A colorless oil, IR (neat): . (cm-1): 3465, 3062, 2925, 1674, 1595, 1450. Data for major isomer. 1H NMR (500 MHz, CDCl3, 25°C): d = 1.12 (d, J = 7.2 Hz, 3H), 2.26 (s, 3H), 2.87 (d, J = 3.8 Hz, OH), 3.93 (m, 1H), 5.45 (m, 1H), 6.86 (d, J = 5.0 Hz, 1H), 7.27 (d, J = 5.0 Hz, 1H), 7.49 (m, 2H), 7.61 (m, 1H), 8.07 (d, J = 7.4 Hz, 2H) ppm. 13C NMR (125 MHz, CDCl3, 25°C): d = 15.4, 45.7, 57.5, 68.2, ISSN 1551-7012 Page 73 ©ARKAT USA, Inc.
