[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH:15]3[CH2:20][CH2:19][C:18](=[O:21])[CH2:17][CH2:16]3)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)#[N:2].C(OCC)C.[BH4-].[Na+].Cl>CO>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C@H:15]3[CH2:20][CH2:19][C@H:18]([OH:21])[CH2:17][CH2:16]3)=[CH:11][CH:10]=2)=[CH:7][CH:8]=1)#[N:2]A suspension of 10 g of 4-(4'-cyano-4-biphenylyl)cyclohexanone, 30 ml of diethyl ether and 270 ml of methanol was treated portionwise at 0° C. with 1.8 g of sodium borohydride. After 3 hours the reaction mixture was made acid (pH 1-2) with 25% hydrochloric acid. The reaction mixture was extracted three times with 50 ml of dichloromethane each time. The combined organic phases were washed twice with 500 ml of water each time and subsequently dried over magnesium sulfate, filtered and concentrated. Recrystallization from methanol gave 3.5 g of trans-4-(4'-cyano-4-biphenylyl)cyclohexanol.
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