Ethyl Methanesulfonate → Ethyl diethylphosphorylmethanesulfonate

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of ethyl methanesulphonate (4.11 ml, 40 mmol) in dry THF (100 ml) was added dropwise at −78° C. 2.5 M n-BuLi in hexane (17.8 ml. 44.4 mmol) within 10 min. After the mixture was stirred for 15 min, ethyl chlorophosphate (3.2 ml, 22.2 mmol) was added slowly at the same temperature. The solution was stirred at −78° C. for 30 min, then allowed to warm to −45° C. and with stirring for additional 1 h. The reaction was quenched by adding 4.4 M NH4Cl solution (11 ml), and the mixture was warmed to ambient temperature. After the organic solvents were removed by a rotary evaporator, the residue was treated with H2O (50 ml), and extracted with DCM (3×70 ml), washed with brine (40 ml) and dried. Evaporation of the solvent under reduced pressure afforded the crude product, which was purified by flash silica gel column chromatography (eluting with 30-100% EtOAc in hexane) to give ethyl diethylphosphorylmethanesulphonate (4.6 g, 80% yield) as light-yellow oil.

Provenance & Evidence