Methanesulfonyl chloride → (2S)-1-(4-cyanophenoxy)-3-methane-sulfonyloxypropan-2-ol
Reaction equation
[C:1]([C:3]1[CH:14]=[CH:13][C:6]([O:7][CH2:8][C@H:9]([OH:12])[CH2:10][OH:11])=[CH:5][CH:4]=1)#[N:2].[CH3:15][S:16](Cl)(=[O:18])=[O:17]>N1C=CC=CC=1>[C:1]([C:3]1[CH:14]=[CH:13][C:6]([O:7][CH2:8][C@H:9]([OH:12])[CH2:10][O:11][S:16]([CH3:15])(=[O:18])=[O:17])=[CH:5][CH:4]=1)#[N:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
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).