Reacción #72585

Ecuación de reacción

methyl(R)-2-hydroxy-2(2-chlorophenyl)acetate

triethylamine

hydrochloric acid

4-nitrobenzenesulfonyl chloride

→

methyl(R)-2-(4-nitrophenylsulfonyloxy)-2(2-chlorophenyl)acetate

Rendimiento 98.0%

Disolventes

dichloromethane

dichloromethane

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe colorless solution obtained
2. 2
   workup.ADDITIONwas added
3. 3
   workup.STIRRINGwhile stirring this mixture
4. 4
   OtroAfter decanting
5. 5
   Lavadothe dichloromethane phase is washed with dilute hydrochloric acid
6. 6
   Concentraciónwith water, before being concentrated under reduced pressure
7. 7
   OtroAn analytically pure sample is obtained
8. 8
   Otroafter purifying on a silica column

Procedimiento

0.72 g (6 mmoles; 0.1 equivalent) of 4-dimethylaminopyridine, 12.0 g (60 mmoles; 1 equivalent) of methyl(R)-2-hydroxy-2(2-chlorophenyl)acetate and 7.8 g (78 mmoles; 1.3 equivalent) of triethylamine and 20 ml of dichloromethane were added to a dry reaction flask. The colorless solution obtained was cooled to 0° C. and then, operating at this temperature, 13.14 g (60 mmoles; 1 equivalent) of 4-nitrobenzenesulfonyl chloride as a solution in 30 ml of dichloromethane was added. The reaction mixture was stirred for 3 hours at 0° C. and 240 ml of 1N hydrochloric acid and 240 ml of dichloromethane was added drop wise, while stirring this mixture. After decanting, the dichloromethane phase is washed with dilute hydrochloric acid and then with water, before being concentrated under reduced pressure. An analytically pure sample is obtained after purifying on a silica column. In this manner, methyl(R)-2-(4-nitrophenylsulfonyloxy)-2(2-chlorophenyl)acetate is obtained: Yield: 98%. Optical purity: 99%.

Fuente