Dichloromethane → methyl 2,2-dimethyl-3-phenyl-3-(3-phenyl-1H-indazol-6-yl)propanoate

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of phenyl(3-phenyl-1H-indazol-6-yl)methanol (67 mg, 0.22 mmol) and (1-methoxy-2-methylprop-1-enyloxy)trimethylsilane (2 mL) in anhydrous dichloromethane (4 mL) was added boron trifluoride diethyl ether complex (0.2 mL, 1.6 mmol) dropwise at 0° C. under argon. After stirred at 0° C. for 15 min, rt for 2 hr, and 40° C. for 1.5 hr, the mixture was poured into saturated aqueous sodium bicarbonate solution at 0° C. The mixture was stirred well and extracted with dichloromethane (10 mL). The dichloromethane layer was dried (Na2SO4) and concentrated. Silica gel flash chromatography gave methyl 2,2-dimethyl-3-phenyl-3-(3-phenyl-1H-indazol-6-yl)propanoate (45 mg, 0.12 mmol, 53% yield) as a glassy solid.

Provenance & Evidence