(1-Methoxy-2-phenylvinyloxy)trimethylsilane → methyl 3-(1H-indazol-5-yl)-2,3-diphenylpropanoate

Participants

Reaction Steps

To a solution of (1H-indazol-5-yl)(phenyl)methyl acetate (245 mg, 0.8 mmol) and (1-methoxy-2-phenylvinyloxy)trimethylsilane (1.78 g, 8.0 mmol, prepared using General Silyl Ketene Acetal Method A) in 20 mL of dry DCM was added TiCl4 (0.8 mL of 1.0 M DCM solution, 0.8 mmol) and then stirred 3 h. The reaction was quenched with MeOH, poured into aqueous sodium bicarbonate and extracted 2×EtOAc. The organic layers were dried over MgSO4, filtered, and concentrated. MPLC purification using a 0-40% EtOAc/hexane gradient gave 170 mg (60% yield) of methyl 3-(1H-indazol-5-yl)-2,3-diphenylpropanoate. MS found: (M+H)+=357.

Provenance & Evidence