Potassium Phosphate, Tribasic → tert-butyl {2-[(1Z)-prop-1-en-1-yl]benzyl}carbamate

Participants

Reaction Steps

A mixed liquid of 1.50 g of tert-butyl(2-bromobenzyl)carbamate, 3.90 g of tripotassium phosphate, 348 mg of dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine, 195 mg of tris(dibenzylideneacetone)dipalladium(0), 905 mg of (1Z)-prop-1-en-1-yl boronic acid, 30 ml of 1,4-dioxane, and 7.5 ml of water was stirred at 90° C. for 15 hours. The reaction mixture was left to be cooled to room temperature and then filtrated over Celite. The filtrate was concentrated under reduced pressure, and then to the reaction mixture was added water, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate and the solvent was then evaporated under reduced pressure. The obtained residue was purified by silica gel chromatography to obtain 1.36 g of tert-butyl {2-[(1Z)-prop-1-en-1-yl]benzyl}carbamate.

Provenance & Evidence