反応 #55459

反応方程式

1,2-dimethoxyethane

n-butyl lithium

ethyl mercaptoacetate

ethyl 3-(1-benzyl-5-methyl-4-imidazolyl)-2-propenoate

1,2-dimethoxyethane

→

ethyl 2-[1-benzyl-5-methyl-4-imidazolyl]-4-oxotetrahydrothiophene

溶媒

hexane

反応条件

後処理

1. 1
   その他at 10° C
2. 2
   workup.WAITis left at room temperature overnight
3. 3
   温度The reaction mixture is cooled in ice
4. 4
   workup.ADDITIONis diluted with 300 ml
5. 5
   ろ過of ether and filtered
6. 6
   workup.DISSOLUTIONThe solid is dissolved in 100 ml
7. 7
   抽出is extracted with a mixture of chloroform and methylene chloride
8. 8
   乾燥The combined extracts are dried over anhydrous sodium sulfate
9. 9
   ろ過filtered
10. 10
    濃縮concentrated in vacuo

実験手順

A solution of ethyl mercaptoacetate (7.45 g., 0.062 mole) in 59 ml. of dry 1,2-dimethoxyethane is cooled to 5° C. and n-butyl lithium (41.3 ml., 0.062 mole) in hexane is added dropwise over 1/2 hour under a nitrogen atmosphere. To this solution is added ethyl 3-(1-benzyl-5-methyl-4-imidazolyl)-2-propenoate (13.0 g., 0.0514 mole) in 50 ml. of 1,2-dimethoxyethane at 10° C. The mixture is stirred at 50°-55° C. for 6 hours and is left at room temperature overnight. The reaction mixture is cooled in ice and is diluted with 300 ml. of ether and filtered. The solid is dissolved in 100 ml. of water and is acidified with dilute hydrochloric acid. The mixture is made basic with sodium bicarbonate and is extracted with a mixture of chloroform and methylene chloride. The combined extracts are dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The product ethyl 2-[1-benzyl-5-methyl-4-imidazolyl]-4-oxotetrahydrothiophene-5-(and/or 3)-carboxylate is obtained as a brown viscous liquid (12.6 g.).

出典