반응 #1960519

반응 방정식

2-(6-hydroxy-naphthalen-2-yl)-propionic acid methyl ester

pyridine

bromoacetyl chloride

→

2-[6-(2-bromo-acetoxy)-naphthalen-2-yl]-propionic acid methyl ester

수율 45.9%

용매

dichloromethane

반응 조건

후처리

1. 1
   세척The reaction mixture was washed with water (500 ml) and 5% solution of sodium carbonate
2. 2
   건조by drying over sodium sulphate and distillation
3. 3
   기타to get crude compound, which
4. 4
   기타was purified by column chromatography

실험 절차

To a solution of 2-(6-hydroxy-naphthalen-2-yl)-propionic acid methyl ester (20 grams) and pyridine (10.3 grams) in dichloromethane (200 ml) maintained at 0-5° C. under N2 atmosphere was added dropwise bromoacetyl chloride (19.6 grams). The reaction was stirred at the same temperature for one hour. The reaction mixture was washed with water (500 ml) and 5% solution of sodium carbonate followed by drying over sodium sulphate and distillation to get crude compound, which was purified by column chromatography using hexane as eluant to get pure 2-[6-(2-bromo-acetoxy)-naphthalen-2-yl]-propionic acid methyl ester (14 grams) as a dark brown syrup. The pure product was characterized using 1H NMR spectroscopy in CDCl3 δ 1.55 (d, 3H, CH3), 3.65 (s, 3H, Ester), 3.82 (q, 1H, CH), 4.08 (s, 2H, OCH2) 7.20 (dd, 1H, Ar), 7.4 (dd, 1H, Ar), 7.57 (d, 1H, Ar), 7.72 (d, 1H, Ar), 7.78 (d, 1H, Ar), 7.84 (d, 1H, Ar).

출처