Ethanol → 2-(4-Ethoxy-3-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Participants

Reaction Steps

To a mixture of 4-hydroxy-3-methoxyphenylboronic acid pinacol ester (Aldrich, Buchs, Switzerland, 200 mg, 0.800 mmol), triphenylphosphine (315 mg, 1.200 mmol) and ethanol (0.056 ml, 0.960 mmol) in THF (4 ml) under Argon was added dropwise diisopropyl azodicarboxylate (0.253 ml, 1.20 mmol). The RM was stirred at it for 17.5 h. Then the RM was diluted with EtOAc and the organic layer was washed with brine (2×), before being dried over Na2SO4, filtered and evaporated. The residue was absorbed on silica gel and purified by MPLC (hexane/EtOAc 0 to 30%). The fractions containing product were together evaporated to give the title compound as a white solid. (HPLC: tR 3.58 min (Method A); M+H=279 MS-ES)

Provenance & Evidence