Tetrahydrofuran → 3-(3-Bromophenyl)pentan-3-ol

反応式

[CH2:1]([Mg]Br)[CH3:2].CO[C:7](=[O:15])[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([Br:14])[CH:9]=1.[Cl-].[NH4+].O1CC[CH2:20][CH2:19]1>>[Br:14][C:10]1[CH:9]=[C:8]([C:7]([OH:15])([CH2:1][CH3:2])[CH2:19][CH3:20])[CH:13]=[CH:12][CH:11]=1

参加物

反応物 4

HCID 8028Tetrahydrofuran

HCID 12070Methyl 3-bromobenzoate

HCID 25517Ammonium Chloride

HCID 178418443HCID 178418443、化合物

生成物 1

HCID 574434823-(3-Bromophenyl)pentan-3-ol

実験手順

Ethylmagnesium bromide (3 mol/l solution in diethyl ether, 34.1 mL, 102.3 mmol) was added to a solution of 3-bromobenzoic acid methyl ester (10 g, 46.51 mmol) in tetrahydrofuran (100 mL) in a nitrogen atmosphere at −78° C. The mixture was stirred at the same temperature for one hour and then heated to room temperature. The reaction mixture was poured into a saturated aqueous ammonium chloride solution, followed by extraction with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and filtered, and the solvent was distilled off under reduced pressure to give crude 3-(3-bromo-phenyl)-pentan-3-ol.