Water → 3-(3-Chloro[1,1'-biphenyl]-2-yl)propan-1-ol

반응식

[Cl:1][C:2]1[C:3]([CH:14]([CH3:18])C(O)=O)=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.O.[O:20]1CCC[CH2:21]1>>[Cl:1][C:2]1[C:3]([CH2:14][CH2:18][CH2:21][OH:20])=[C:4]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:5]=[CH:6][CH:7]=1

참가 물질

반응물 3

HCID 962Water

HCID 8028Tetrahydrofuran2회

HCID 20403362HCID 20403362, 화합물

생성물 1

HCID 204033423-(3-Chloro[1,1'-biphenyl]-2-yl)propan-1-ol

실험 절차

Under a dry argon atmosphere, borane-tetrahydrofuran complex (230 ml of a 1.5 M solution in tetrahydrofuran) was added dropwise to a stirred solution of (3-chloro[1,1'-biphenyl]-2-ylpropanoic acid (40.0 g, 0.15 mole) in tetrahydrofuran (250 ml). The reaction mixture was stirred at room temperature for approximately 18 hours. Water (30 ml) was then added to the reaction mixture during a 0.5 hour period. The solvent was removed from the mixture under reduced pressure to yield an oil. The oil was partitioned betwen methylene chloride and dilute aqueous sodium hydroxide. The organic phase was separated, dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated under reduced pressure to yield 3-(3-chloro[1,1'-biphenyl]-2-yl)-1-propanol as an oil.