Water → HCID 21200954, compound

Participants

Reaction Steps

To a solution of 26-3 (0.391 g, 1.75 mmol) in methylene chloride (6 ml) cooled in an ice-bath in a 3-necked round bottom flask equipped with a nitrogen inlet and rubber septum was added 1.0M boron tribromide in methylene chloride (3.9 ml, 3.9 mmol) via syringe. The resulting mixture was stirred 18 h while warming to ambient temperature. Water (7 ml) was added and the mixture was extracted with ether (35 ml). The organic fraction was washed with brine (10 ml), dried (sodium sulfate), and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with ethyl acetate/hexane (1:5 increasing to 1:3), to give product 26-4 as a white solid, mp: 163°-164° C.

Provenance & Evidence