Ethyl Acetate → HCID 59138592, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of (6-chloropyridin-3-yl)(phenyl)methyl acetate (0.52 g, 2.0 mmol) and (1-methoxy-2-methylprop-1-enyloxy)trimethylsilane (2.0 mL, 9.8 mmol) in anhydrous dichloromethane (10 mL) was added titanium tetrachloride solution (1M in toluene, 4.4 mL, 4.4 mmol) dropwise at 0° C. under argon. After stirring at 0° C. for 48 hrs (refrigerator) and room temperature for 5 hours, the mixture was poured into a saturated aqueous sodium bicarbonate solution (40 mL) maintained at 0° C. The mixture was extracted with ethyl acetate (2×40 mL). The combined organic solutions were dried (Na2SO4) and concentrated. Silica gel flash chromatography (0-100% ethyl acetate in hexanes) gave methyl 3-(6-chloropyridin-3-yl)-2,2-dimethyl-3-phenylpropanoate (0.48 g, 1.6 mmol, 80% yield) as a colorless liquid. MS found: (M+H)+=304.25.

Provenance & Evidence