Water → HCID 11805970, compound

Participants

Reaction Steps

Tetrabutylammonium fluoride (0.5 mL of a 1.0M solution in tetrahydrofuran) was added to a solution of alcohol 2 (65 mg, 0.23 mmol) in tetrahydrofuran (5 mL) under nitrogen. After two hours water was added to the solution and the resulting mixture extracted with dichloromethane. The combined organic extracts were washed with brine and dried over MgSO4. After filtration and removal of the solvents under reduced pressure, chromatography with 5% ethyl acetate in petrol gave sulfide 3 (31 mg, 64%), [a]20D−90.5 (c 2.10 in CHCl3); umax (thin film)/cm−1 3483 (OH), 2942 (CH), 1701 (C═C), 1627 (C═C); dH (250 MHz; CDCl3) 0.97 (3H, s, CH3), 1.01-1.16 (1H, m), 1.27 (3H, s, CH3), 1.50-1.83 (4H, m), 1.96-2.10 (2H, m), 2.14 (1H, br s, OH), 2.52 (1H, d, J 9.0, CHHS), 3.22 (1H, d, J 9.0, CHHS), 4.93 (1H, d, J 1.0, ═CHH), 5.12 (1H, d, J 1.0, ═CHH); dC (63 MHz; CDCl3) 22.02 (CH3), 22.05 (CH3), 26.89 (CH2), 31.95 (CH2), 32.07 (CH2), 37.38 (CH2), 46.25 (C), 50.79 (CH), 61.68 (C), 93.20 (C), 101.39 (CH2), 151.81 (C); m/z (EI) 210 (M+, 30%), 108 (57), 95 (100), 81 (27), (Found; M+, 210.1085. C12H18OS requires 210.1078).

Provenance & Evidence