3-Benzyloxy-phenylboronic acid → 1,3,5-Trimethoxybenzene

Participants

Reaction Conditions

Reaction Steps

To a 4 ml reaction vial equipped with a magnetic tumble stir disc under N2 atmosphere was charged (E)-methyl 3-cyclopropyl-2-methyl-3- (tosyloxy)acrylate 3-(E) (40.0 mg, 0.129 mmol), (3-(benzyloxy)phenyl)boronic acid 4 (32.3 mg, 0.142 mmol), palladium precatalyst 5 (5.96 mg, 6.44 µmol) and 1,3,5-trimethoxybenzene (2.17 mg, 0.013 mmol). ACN (1000 µl) and water (10 µl) were added and the mixture agitated to dissolve all solids. To a 40 ml vial was charged K3PO4 (2.12 g, 10.0 mmol) and water to dilute to 10 ml. The resulting 1 M aqueous K3PO4 solution was then sparged with N2 gas for 30 min in preparation for automated dispensing (387 µl, 0.387 mmol). Finally, to a 96-well sample dilution plate was charged 400 µl of a 9:1 mixture of acetonitrile and aqueous pH 3.5 ammonium formate buffer.

Provenance & Evidence