تفاعل #322745

معادلة التفاعل

hydrochloric acid

sodium bis(2-methoxyethoxy)aluminum hydride

morpholine

N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfonamide

→

N-[(4,6-Dimethoxypyrimidin-2-yl)aminocarbonyl]-2-formylbenzenesulfonamide

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةto warm to room temperature over a period of 2 hours
2. 2
   استخلاصthe mixture was extracted with methylene chloride
3. 3
   غسيلThe organic extracts were washed
4. 4
   أخرىdried
5. 5
   أخرىevaporated
6. 6
   أخرىthe unreacted ester and the over-reduced alcohol, was purified by means of dry column chromatography

الإجراء التجريبي

A mixture of 3.0 g of sodium bis(2-methoxyethoxy)aluminum hydride and 0.9 g of morpholine in 25 ml of dry tetrahydrofuran was cooled to -40° C. and 1.0 g of N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2-methoxycarbonylbenzenesulfonamide was added. The resulting clear homogeneous solution was allowed to warm to room temperature over a period of 2 hours. Dilute hydrochloric acid was added and the mixture was extracted with methylene chloride. The organic extracts were washed, dried and evaporated. The crude product, which contained the desired aldehyde, the unreacted ester and the over-reduced alcohol, was purified by means of dry column chromatography. The purified product had a m.p. of 180° C.

المصدر