Sodium borohydride → 4-(2'-Fluoro-4-biphenylyl)-4-hydroxy-butyric acid
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:20])[CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:10][CH:9]=1.[BH4-].[Na+]>[OH-].[K+].O>[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:20])[CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:10][CH:9]=1Participants
Procedure
45.9 gm (0.169 mol) of 4-(2'-fluoro-4-biphenylyl)-4-oxo-butyric acid were dissolved in a solution of 11.2 gm of potassium hydroxide in 450 ml of water at 35° C. While stirring, a solution of 6.4 gm (0.169 mol) of sodium borohydride in water was added. After stirring for about 3 hours, the mixture was acidified and extracted with ethyl acetate. From the washed and dried organic phase, the cyclohexylamine salt was precipitated by addition of cyclohexylamine. Yield: 41 gm (65% of theory); m.p. 174°-175° C.; melting point of the free acid: 120°-122° C. (from benzene); melting point of the isobutylamine salt: 125°-127° C. (from isopropanol); melting point of the morpholine salt: 108°-110° C. (from isopropanol); melting point of the sodium salt: 222°-224° C. (from ethanol).
Workup
- stirringAfter stirring for about 3 hours
- extractionextracted with ethyl acetate
- washFrom the washed
- customdried organic phase, the cyclohexylamine salt was precipitated by addition of cyclohexylamine
- custom120°-122° C. (from benzene)
- custom125°-127° C. (from isopropanol)
- custom108°-110° C. (from isopropanol)
- custom222°-224° C. (from ethanol)
Sources & evidence
- ORD record
- ord-6d6eb758cfde4d8eb57057276664e353
- Source dataset
- uspto-grants-1977_05
- Patent number
- US04021479
Reaction notes
Loading…