Triethylamine → Methyl 2-(4-chlorophenyl)acrylate

참여 물질

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Methyl 2-(4-chlorophenyl)-3-hydroxypropanoate (16.2 g, 75.5 mmol) was dissolved in DCM (200 mL). Triethylamine (26.3 mL, 188.7 mmol) was then added, and the solution was cooled to 0° C. The solution was then treated with methanesulfonyl chloride (5.84 mL, 75.5 mmol), and the mixture was stirred at 0° C. for 30 minutes. The cold solution was acidified to a pH of 1, and extracted with methylene chloride. The combined organic layers were washed with 1N HCl, water, 6% NaHCO3, dried over Na2SO4 and concentrated. The crude oil was filter chromatographed on SiO2 (with gypsum, Aldrich 28,852-7, 350 g) and eluted with 20:1 hexane:EtOAc to give methyl 2-(4-chlorophenyl)acrylate (10.9 g, 73%).

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