Methanol → Ethyl 4-(2'-fluoro-4-biphenylyl)-4-hydroxy-butyrate

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:22])[CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:10][CH:9]=1.CO.[BH4-].[Na+]>>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([OH:22])[CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:10][CH:9]=1

Participants

Reactant 3

HCID 887Methanol

HCID 4311764Sodium borohydride

HCID 21437951Ethyl 4-(2'-fluoro-4-biphenylyl)-4-oxo-butyrate

Product 1

HCID 21437975Ethyl 4-(2'-fluoro-4-biphenylyl)-4-hydroxy-butyrate

Procedure

To a solution of 15 gm (0.05 mol) of ethyl 4-(2'-fluoro-4-biphenylyl)-4-oxo-butyrate in 100 ml of methanol 1.9 gm (0.05 mol) of sodium borohydride were added at a temperature between 0° and 5° C., while stirring. The precipitate was vacuum-filtered off and dissolved in ether. The ethereal solution was washed with an aqueous sodium bicarbonate solution and then with water, dried and evaporated. The residual oil was recrystallized from cyclohexane. Yield: 12 gm (79.5% of theory), m.p. 61°-62° C.