반응 #72585

반응 방정식

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

triethylamine

hydrochloric acid

4-nitrobenzenesulfonyl chloride

→

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

수율 98.0%

용매

dichloromethane

dichloromethane

dichloromethane

반응 조건

후처리

1. 1
   기타The colorless solution obtained
2. 2
   workup.ADDITIONwas added
3. 3
   workup.STIRRINGwhile stirring this mixture
4. 4
   기타After decanting
5. 5
   세척the dichloromethane phase is washed with dilute hydrochloric acid
6. 6
   농축with water, before being concentrated under reduced pressure
7. 7
   기타An analytically pure sample is obtained
8. 8
   기타after purifying on a silica column

실험 절차

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%.

출처