Methanesulfonyl chloride → (2S)-1-(4-cyanophenoxy)-3-methane-sulfonyloxypropan-2-ol

Participants

Reaction Steps

57.2 g of (2R)-3-(4 cyanophenoxy)propane-1,2-diol was dissolved in dry pyridine, (300 ml) and treated dropwise with methanesulfonyl chloride, (20.7 ml), at -10° C. The reaction mixture was kept at 5° C. overnight, evaporated at reduced pressure and poured on ice and 2 M hydrochloric acid. The solid precipitate was recrystallized three times from methanol to yield 12.3 g of the title compound, m.p. 119°-121° C., [α]D20 +9.7° (c 1.0, CH3OH).

Provenance & Evidence