Dimethyl Sulfoxide → HCID 13731466, compound

Participants

Reaction Conditions

Reaction Steps

To a complex prepared at -60° C. from the addition of 10.4 ml of dry dimethyl sulfoxide to 8.9 g (70 mmol) of oxalyl chloride in 150 ml of methylene chloride, was added, dropwise, 27.7 g (62.2 mmol) of the compound prepared in (a) above. After stirring the mixture under a nitrogen atmosphere for 1 hour, 50 ml of triethylamine in 50 ml of methylene chloride was added and the resultant mixture was allowed to warm to 0° C. over a period of 30 minutes, after which time it was quenched with 75 ml of water. After the mixture was allowed to warm to room temperature, the organic layer was separated, washed with a saturated sodium chloride solution, dried over magnesium sulfate and concentrated in vacuo to afford an oil which solidified on standing. Flash chromatography on silica gel employing a mixture of petroleum ether and diethyl ether in a ratio of 7:3 as the eluent yielded a solid, m.p. 33°-34° C.

Provenance & Evidence