تفاعل #1321

معادلة التفاعل

6-iodonicotinic acid

ethanol

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

→

title compound

Ethyl 6-iodonicotinoate

المذيبات

dichloromethane

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   تركيزconcentrated in vacuo
2. 2
   أخرىpartitioned between 200 ml of water and 250 ml of ethyl ether
3. 3
   أخرىthe layers were separated
4. 4
   غسيلThe aqueous phase was washed with 2×150 ml-portions of ethyl ether
5. 5
   غسيلwashed once with 75 ml of brine solution
6. 6
   تجفيفdried over MgSO4
7. 7
   ترشيحfiltered
8. 8
   تركيزconcentrated in vacuo to a yellow solid
9. 9
   أخرىPurification by flash chromatography (silica, 10% ethyl acetate in hexane)

الإجراء التجريبي

To a suspension of 23.38 g (94.2 mmol) of 6-iodonicotinic acid in 100 ml of dichloromethane was added a solution of 19.86 g (103.6 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride in 250 ml of dichloromethane. To this suspension was added 12.40 g (15.8 ml, 269.3 mmol) of ethanol (95%) and 1.15 g (9.4 mmol) of 4-dimethylaminopyridine. The resulting solution mixture was then heated at 50° C. in an oil bath for 24.5 hours, concentrated in vacuo, partitioned between 200 ml of water and 250 ml of ethyl ether, and the layers were separated. The aqueous phase was washed with 2×150 ml-portions of ethyl ether. All organic phases were combined, washed once with 75 ml of brine solution, dried over MgSO4, filtered and concentrated in vacuo to a yellow solid. Purification by flash chromatography (silica, 10% ethyl acetate in hexane) yielded the title compound as a white solid.

المصدر