Hydrochloric Acid → (2RS,3RS)-2-(2,4-difluorophenyl)-3-mercapto-1-(1H-1,2,4-triazol-1-yl)-2-butanol

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Reaction Steps

A methanol (2.0 ml) solution containing (2RS,3RS)-2-(2,4-difluorophenyl)-3-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)oxirane (0.05 g), methyl 3-mercaptopropionate (0.11 ml) and a 28% sodium methylate-methanol solution (0.14 ml) was refluxed for 1.0 hour. The reaction mixture was cooled, to which was added water (10 ml). The mixture was neutralized with 1N aqueous solution of hydrochloric acid, followed by extraction with methylene chloride (5.0 ml×twice). The extract solution was dried over anhydrous sodium sulfate, then the solvent was distilled off. The residue was subjected to a silica gel chromatography (2.5 cm×5 cm), followed by elution with ethyl acetate-hexane (1:2). The object fraction was concentrated, to which was added ethyl acetate to give (2RS,3RS)-2-(2,4-difluorophenyl)-3-mercapto-1-[(1H)-1,2,4-triazol-1-yl]-2-butanol (0.030 g) as colorless needles.

Provenance & Evidence