Hexane → Sodium diethyl phosphite

Participants

Reaction Conditions

Reaction Steps

A fresh solution of sodium diethyl phosphite was prepared from sodium hydride and diethyl phosphite in tetrahydrofuran at a concentration of 2 milliequivalents/ml and added, as described below, to a solution of 260 mg of 2,5-anhydro-2-C-[(phenylmethoxy)methyl]-3,4,6-tris-O-(phenylmethyl)-D-glucitol, 1-(trifluoromethanesulfonate) in 1 ml of tetrahydrofuran. A 0.5 ml portion of the stock solution was added and the mixture stirred 1.5 hours; 0.25 ml was added and stirring continued for 2.5 hours; 0.22 ml was added, the mixture warmed to 45° C. for 20 minutes then cooled to room temperature. The mixture was worked up with hexane, ether and water, giving an oil. This oil was purified by flash chromatography, eluting with 1% methanol in dichloromethane, giving 203 mg of the desired compound.

Provenance & Evidence