反応 #1321

反応方程式

6-iodonicotinic acid

ethanol

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

→

title compound

Ethyl 6-iodonicotinoate

溶媒

dichloromethane

dichloromethane

反応条件

後処理

1. 1
   濃縮concentrated in vacuo
2. 2
   その他partitioned between 200 ml of water and 250 ml of ethyl ether
3. 3
   その他the layers were separated
4. 4
   洗浄The aqueous phase was washed with 2×150 ml-portions of ethyl ether
5. 5
   洗浄washed once with 75 ml of brine solution
6. 6
   乾燥dried over MgSO4
7. 7
   ろ過filtered
8. 8
   濃縮concentrated in vacuo to a yellow solid
9. 9
   その他Purification by flash chromatography (silica, 10% ethyl acetate in hexane)

実験手順

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.

出典