Tetrahydrofuran → HCID 18969768, compound
Reaction equation
CO[C:3]1([CH2:24]CCC)[C:6](=[O:7])[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:4]1[C:14]1[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:34]1COCC1>>[CH3:24][C:3]1([CH3:34])[CH:6]([OH:7])[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:4]1[C:14]1[CH:15]=[CH:16][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:18][CH:19]=1Participants
4
Conditions
- Temperature
- 0 °C
Procedure
To a solution of Example 14 (100 mg) in THF (1 mL) at 0° C., was added LAH (1M, THF, 920 μL). The mixture was stirred at 0° C. for min., quenched with H2O, and diluted with EtOAc. The organic phase was washed with HCl 1N, brine, dried (MgSO4) and the solvents evaporated. The residue was purified by flash chromatography (silica gel; hexane/EtOAc (70:30)) to give the title compound as a white solid, m.p. 79°-81° C.