Ethanol → HCID 22144811、化合物
反応式
[O:1]=[C:2]([C:8]1[C:16]2[O:15][CH:14]=[CH:13][C:12]=2[CH:11]=[C:10]([F:17])[CH:9]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[BH4-].[Na+].[CH2:20]([OH:22])[CH3:21]>>[C:20]([O:1][CH:2]([C:8]1[C:16]2[O:15][CH:14]=[CH:13][C:12]=2[CH:11]=[C:10]([F:17])[CH:9]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4])(=[O:22])[CH3:21]参加物
4
実験手順
A mixture of 0.894 gm (3.78 mMol) ethyl 2-oxo-2-(5-fluorobenzofur-7-yl)acetate and 0.143 gm (3.78 mMol) sodium borohydride in 5 mL ethanol was stirred at room temperature for 1 hour. The reaction was quenched by the dropwise addition of water and was then concentrated under reduced pressure. The residue was dissolved in ethyl acetate, washed with water, and the organic phase concentrated under reduced pressure. The residual oil was subjected to flash silica gel chromatography, eluting with chloroform containing 2% methanol. Fractions containing ethyl 2-hydroxy-2-(5-fluorobenzofur-7-yl)acetate were combined and concentrated under reduced pressure. This residue was dissolved in 2.5 mL of pyridine and 2.5 mL acetic anhydride and was stirred at room temperature for 1 hour. The reaction mixture was then diluted with 25 volumes of ethyl acetate, washed with water, and concentrated under reduced pressure to provide 0.675 gm (64%) of the desired compound.