Dimethyl Sulfoxide → HCID 57003203, compound

Participants

Reaction Steps

A solution of 1.1 g of oxalyl chloride in 15 ml of methylene chloride is cooled to -65°-70° under argon and within a period of 2 minutes 1.5 g of dimethyl sulfoxide in 5 ml of methylene dichloride are added. After stirring for 10 minutes at -65°-70°, 1.7 g of (2R,3R)-2,3-epoxy-3-(3-trifluoromethylphenyl)-propanol in 15 ml of methylene chloride are added dropwise. After stirring for a further 30 minutes, 4 g of triethylamine are added dropwise, the temperature rising to -40°. The temperature is allowed to rise to 0° and the reaction mixture is poured onto phosphate buffer (pH 8). The organic phase is separated off and the aqueous phase is extracted with methylene chloride. The combined organic extracts are washed twice with brine, dried over sodium sulfate and concentrated by evaporation. Chromatography of the residue on silica gel with hexane/ethyl acetate (7:3) yields the title compound in the form of a colourless oil; IR (methylene chloride): 2820, 1730, 1330, 1165, 1125, 1070 cm-1. Rf =0.36 (hexane/ethyl acetate 3:2). [α]D20 (chloroform, 0.20%)=-17.5°±5°.

Provenance & Evidence