تفاعل #2139941

معادلة التفاعل

HCl

N-hydroxy-5-norbornene-2,3-dicarboximide

pyridine

2-chloroethanesulfonyl chloride

→

product

المردود 73.0%

N-(2-chloroethanesulfonyloxy)-5-norbornene-2,3-dicarboximide

المردود 73.0%

المذيبات

CH2Cl2

ethyl acetate

ظروف التفاعل

المعالجة

1. 1
   أخرىThe layers are separated
2. 2
   استخلاصthe aqueous layer is extracted once with ethyl acetate (280 ml)
3. 3
   تجفيفThe combined organic extracts are dried over Na2SO4
4. 4
   أخرىevaporated under reduced pressure
5. 5
   أخرىleaving a colorless oil which
6. 6
   أخرىfurther dried under vacuum

الإجراء التجريبي

A solution of 12.5 g (70.0 mmol) of N-hydroxy-5-norbornene-2,3-dicarboximide and pyridine (6.2 ml, 77.0 mmol) in CH2Cl2 (105 ml) is treated dropwise with 2-chloroethanesulfonyl chloride (7.36 ml, 70.0 mmol) at 0° C., according to the procedure of W. C. Groutas, M. A. Stanga, J. C. Castrisos, E. J. Schatz, M. J. Brubaker J. Pharm. Sci. 1990, 79, 886-88. After stirring overnight at room temperature, the reaction mixture is diluted with ethyl acetate (280 ml) and then treated with 5% aqueous HCl (130 ml). The layers are separated and the aqueous layer is extracted once with ethyl acetate (280 ml). The combined organic extracts are dried over Na2SO4 and evaporated under reduced pressure, leaving a colorless oil which solidifies when further dried under vacuum. 15.6 g (73%) of the product are obtained as a white solid.

المصدر