反应详情

To a solution of 6-(6-hydroxy-5-methyl-5-phenylhexylsulfanyl)-2-methyl-2-phenylhexan-1-ol (3.0 g, 7.0 mmol) in glacial acetic acid (20 mL) was added hydrogen peroxide (50 wt. % in water; 0.5 mL, 7.0 mmol). The reaction mixture was stirred at rt for 22 h, then diluted with water (100 mL), and extracted with chloroform (3×80 mL). The combined organic phases were subsequently washed with saturated NaHCO3 solution (3×80 mL) and saturated NaCl solution (80 mL), dried over MgSO4, concentrated in vacuo, and dried in high vacuo to give crude 6-(6-hydroxy-5-methyl-5-phenylhexylsulfinyl)-2-methyl-2-phenylhexan-1-ol (2.63 g 88%) as an oil. 1H NMR (300 MHz, CDCl3/TMS): δ (ppm): 7.42-7.12 (m, 10 H), 3.78-3.58 (m, 2 H), 3.58-3.45 (m, 2 H), 2.90-2.70 (m, 2 H), 2.68-2.39 (m, 2 H), 1.95-1.50 (m, 8 H), 1.50-1.00 (m, 10 H). 13C NMR (75 MHz, CDCl3/TMS): δ (ppm): 144.5, 144.4, 128.4, 128.3, 126.5, 126.2, 126.1, 72.2, 72.1, 71.9, 52.4, 52.0, 43.2, 37.8, 37.7, 23.2, 22.9, 22.4, 21.7, 21.5. HRMS (LSIMS, nba): Calcd. for C26H39O3S1 (MH+): 431.2620, found: 431.2611.

1. extractionextracted with chloroform (3×80 mL)
2. washThe combined organic phases were subsequently washed with saturated NaHCO3 solution (3×80 mL) and saturated NaCl solution (80 mL)
3. dry with materialdried over MgSO4
4. concentrationconcentrated in vacuo
5. customdried in high vacuo