Benzoyl chloride → HCID 14347867, compound

Participants

Reaction Steps

To a stirred, ice-cooled solution of (B) (3.7g.,0.025m.) in dried pyridine (30 ml.) was added dropwise over ca. 5 minutes under a nitrogen atmosphere a solution of benzoyl chloride (3.0 ml., 0.026m.) in dry ether (5 ml.). The mixture was stirred for an additional 5 minutes, the ice-bath removed, and the mixture allowed to stir at ambient temperatures. After ca.1.5 hr., tlc analysis indicated that the reaction was complete and the mixture was transferred to a separatory funnel with ether (300 ml.). The mixture was washed IX with water (100 ml.), 4 X with saturated copper sulfate solution, lX with saturated sodium chloride solution and dried over sodium sulfate. Concentration of the filtered solution followed by chromatography on silica gel (200g.; 1% methanol/methylene chloride as eluant) yielded 5.4g (C) as an oil. N.m.r. was consistent with the structure [α]D =30 9.1 (c=0.75, CDCl3).

Provenance & Evidence