Hydrochloric Acid → 4-(2-(Tert-butyldimethylsilyloxy)ethyl)-3-ethylphenylboronic acid

Participants

Reaction Conditions

Reaction Steps

n-Butyl Lithium (4.7 mL) was added to a solution of 46A (2.1 g, 6.1 mmol) in THF at −78° C. After stirring to 10 min at −78° C., trimethyl borate (1.0 mL, 12.3 mmol) was added dropwise. After warming to ambient temperature, the reaction mixture was stirred an additional 2 h. HCl (1.0 M, 30 mL, aqueous) was added to the mixture at −40° C. and stirred at −20° C. for 30 min. The solution was extracted with diethyl ether. The combined organics were washed with brine, dried over Na2SO4 and concentrated in vacuo. The resulting oil was purified by flash chromatography (0% to 20% MeOH in CH2Cl2) to yield 46B (0.90 mg, 48%) as a clear oil. MS (ESI) m/z 307.4 (M−H)−.

Provenance & Evidence