Diethyl Ether → HCID 23182903, compound

Participants

Reaction Steps

55 ml (39 mmoles) of a 0.71 M solution of 4-phenoxybutyl magnesium bromide prepared from 10.1 g (44 mmoles) of 4-phenoxy bromide and 1.07 g (44 mmoles) of magnesium in 60 ml of ether was taken, and in an atmosphere of nitrogen, a solution of 7.63 g (36 mmoles) of 4-t-butyldimethylsilyloxy-2-cyclopentenone in 20 ml of ether was added dropwise at -78° C., and the mixture was stirred for 4 hours. A saturated aqueous solution of sodium chloride was added to terminate the reaction. The reaction mixture was extracted with ether, washed with an aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was chromatographed on a silica gel column (hexane:AcOEt=12:1) to give 5.2 g (40%) of a low polarity, 1,2-adduct and 2.9 g (22%) of a high polarity 1,2-adduct. ##STR30##

Provenance & Evidence