Sodium borohydride → Tert-butyl 3-(4-((2'-(hydroxymethyl)biphenyl-3-yl)methoxy)phenyl)propanoate

反応式

[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[CH:19][CH:18]=2)[CH:10]=1)=[O:2].[BH4-].[Na+]>CO.O1CCCC1>[OH:2][CH2:1][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][O:16][C:17]2[CH:18]=[CH:19][C:20]([CH2:23][CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[CH:21][CH:22]=2)[CH:10]=1

参加物

実験手順

tert-Butyl 3-(4-(2′-formylbiphenyl-3-ylmethoxy)phenyl)propanoate (0.30 g, 0.72 mmol) was dissolved in a mixed solution of methanol (6 mL) and tetrahydrofuran (6 mL), and sodium borohydride (14 mg, 0.36 mmol) was added under ice-cooling, and the mixture was stirred at the same temperature for 2 hrs. The reaction mixture was concentrated, and the residue was diluted with ethyl acetate, washed with 1N hydrochloric acid and saturated brine, dried, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-1/1) to give the title compound (0.25 g, yield 83%) as a colorless oil.