Acetyl chloride → HCID 21245915, compound

Participants

Reaction Steps

To 0.259 g (0.5 mmol) of the compound prepared in (b) above dissolved in 3 ml of chloroform was added, with stirring and under a nitrogen atmosphere, 0.393 g (5.0 mmol) of acetyl chloride. The resultant mixture was cooled in an ice bath and to the cooled mixture was added, dropwise, 0.51 g (5.0 mmol) of triethylamine. The resultant solution was then warmed to reflux and maintained at the reflux temperature for 2 hours. The volatiles were then removed under high vacuum and the resultant residue was dissolved in methylene chloride and washed rapidly with a saturated aqueous sodium bicarbonate solution. The organic layer was then dried over sodium sulfate, filtered and concentrated. The resultant residue was then chromatographed on silica gel employing, successively as the eluents, a mixture of petroleum ether and ethyl acetate in a ratio of 4:1 by volume initially, with the product being eluted when the eluent was at a ratio of 7:3 by volume. The resultant solution was then concentrated to yield an oil.

Provenance & Evidence