Hydrochloric Acid → 4-(1-(Tert-butyldimethylsilyloxy)propan-2-yl)phenylboronic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of 73C (100 mg in 2 mL dry THF, 0.3 mmol) at −78° C. was added n-BuLi (1.6 M, 0.2 mL, 0.32 mmol), followed by B(OMe)3 (0.1 mL, 0.9 mmol). The solution was stirred at −78° C. for 2 h. 1N HCl (4 mL) was added, and stirred 30 min. The mixture was extracted with EtOAc (3×20 mL). The organic layer washed by brine, dried (Na2SO4). Purification through ISCO (0-80% EtOAc in hexanes) gives 73D (37 mg, 40%). 1H NMR (400 MHz, Chloroform-d) δ ppm −0.03 (d, J=3.52 Hz, 6 H) 0.84-0.89 (m, 9 H) 1.33 (d, J=7.03 Hz, 3H) 2.92-3.06 (m, 1 H) 3.62-3.79 (m, 2 H) 7.36 (d, J=7.91 Hz, 2 H) 8.16 (d, J=7.91 Hz, 2 H)

Provenance & Evidence