Benzyl Bromide → HCID 21264715, compound

Participants

Reaction Steps

Under a stream of argon, 212 mg (5.31 mmol, 2.40 equivalents) of an oily dispersion of 60% sodium hydride was washed with hexane to remove the oil component. While the dispersion kept cooled with cold water, 11.0 ml of dry dimethyl sulfoxide was added and stirred. To this, was added 500 mg (2.21 mmol) of 2-methylpropyl-(2,3,4,6-tetrahydroxyphenyl) ketone (9) and stirred for 40 minutes. To the produced mixture, 0.525 ml (4.42 mmol, 2.00 equivalents) of benzyl bromide was added dropwise and stirred for four hours. The resultant mixture was combined with 10 ml of a saturated aqueous ammonium chloride solution and extracted by ether. The organic layer was washed with saturated brine, dried over sodium sulfate, concentrated under a reduced pressure, and subjected to silica gel chromatography (100 g of Wako Gel C-200, eluted with hexane:ethyl acetate=3:2) to obtain 207 mg (yield 23.1%) of the product (33) in the form of yellow powdery crystals.

Provenance & Evidence