Diethyl Ether → HCID 15190126, compound

Participants

Reaction Steps

In a mixed solvent of 100 ml of THF and 30 ml of water was dissolved 10.0 g (20.0 mmol) of 2-(2,4-difluorophenyl)-2-hydroxy-3-((4-methoxyphenyl)methylthio)-3-methylbutyl (S)-(+)-2-phenylpropionate ([α]25 +15.9° (c=1.09, MeOH)), and 1.68 g (40.0 mmol) of lithium hydroxide monohydrate was added thereto in divided portions with stirring under ice-cooling. The mixture was warmed to room temperature and stirred for 30 hours. To the reaction mixture was added diethyl ether, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with a saturated sodium hydrogencarbonate aqueous solution and a saturated sodium chloride aqueous solution and dried. The solvent was removed by distillation under reduced pressure, and the residue was subjected to column chromatography using a mixed solvent of hexane and ethyl acetate (5:1) as an eluent. The solvent was removed by distillation under reduced pressure to obtain 7.3 g (99%) of (+)-2-(2,4-difluorophenyl)-3-((4-methoxyphenyl)methylthio)-3-methylbutane-1,2 -diol as a colorless oily substance.

Provenance & Evidence