Hydrochloric Acid → HCID 178442265, compound

Participants

Reaction Steps

Under a stream of argon, 440 mg (11.0 mmol, 3.01 equivalents) of an oily dispersion of 60% sodium hydride was washed with hexane to remove the oil component. The dispersion kept cooled with cold water and 18.0 ml of dry dimethyl sulfoxide added were stirred together. To the stirred suspension, 900 mg (3.66 mmol) of phenyl-(2,3,4,6-tetrahydroxyphenyl) ketone (10) was added and stirred for 30 minutes. Further, 0.830 ml (7.32 mmol, 2.00 equivalents) of 1-chloro-3-methyl-2-butene was added dropwise stirring for two hours. The produced mixture was combined with 15 ml of a saturated aqueous ammonium chloride solution and 2 ml of 2 M hydrochloric acid 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 (g of Wako Gel C-200, eluted with hexane ethyl acetate 4:1) to obtain 716 mg (yield 51.3%) of the product (32) in the form of yellow powdery crystals.

Provenance & Evidence