CO.[OH:3][C:4]1([CH3:18])[CH2:9][CH:8]([OH:10])[CH2:7][C:6]([CH3:12])([CH3:11])[CH:5]1[CH:13]=[CH:14][C:15](=[O:17])[CH3:16].[BH4-].[Na+]>C(O)(=O)C>[OH:3][C:4]1([CH3:18])[CH2:9][CH:8]([OH:10])[CH2:7][C:6]([CH3:11])([CH3:12])[CH:5]1[CH:13]=[CH:14][CH:15]([OH:17])[CH3:16]To 20 ml of a methanol solution containing 200 mg of 4-(2,4-dihydroxy-2,6,6-trimethylcyclohexyl)but-3-en-2-one was added 40 mg of sodium borohydride under ice-cooling, and the mixture was stirred at room temperature for 5 hours. After completion of the reaction, the reaction mixture was treated with acetic acid, and the solvent, etc. were removed by distillation under reduced pressure. Ethyl acetate was added to the residue, followed by washing with a saturated sodium chloride aqueous solution and then, with water. The organic layer was dried over magnesium sulfate, and the ethyl acetate was removed by distillation. The residue was purified by silica gel column chromatography to obtain 646 mg (yield: 73%) of 4-(2,4-dihydroxy-2,6,6-trimethylcyclohexyl)but-3-en-2-ol.
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