1,2-Dimethoxyethane → Ethyl 2-(1-benzyl-5-methyl-4-imidazolyl)-4-oxotetrahydrothiophene

HRID 27181

反応式

HRID 27181 の反応式
[SH:1][CH2:2][C:3]([O:5]CC)=O.[CH3:8]OCCOC.C([Li])CCC.[CH2:19]([N:26]1[C:30]([CH3:31])=[C:29]([CH:32]=[CH:33][C:34](OCC)=O)[N:28]=[CH:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CCCCCC>[CH2:33]([C:32]1([C:29]2[N:28]=[CH:27][N:26]([CH2:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:30]=2[CH3:31])[CH2:8][C:3](=[O:5])[CH2:2][S:1]1)[CH3:34]

参加物

6

反応物 4

HCID 80711,2-Dimethoxyethane2 回HCID 12185Ethyl ThioglycolateHCID 54025209Ethyl 3-(1-benzyl-5-methyl-4-imidazolyl)-2-propenoateHCID 178418339Butyllithium

生成物 1

HCID 86737180Ethyl 2-(1-benzyl-5-methyl-4-imidazolyl)-4-oxotetrahydrothiophene

試薬・触媒・溶媒 1

HCID 8058Hexane溶媒

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.).

後処理

  1. customat 10° C
  2. waitis left at room temperature overnight
  3. temperatureThe reaction mixture is cooled in ice
  4. additionis diluted with 300 ml
  5. filtrationof ether and filtered
  6. dissolutionThe solid is dissolved in 100 ml
  7. extractionis extracted with a mixture of chloroform and methylene chloride
  8. dry with materialThe combined extracts are dried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-43635b8c0f004ae4ab0630f6b70e2e18
出典データセット
uspto-grants-1980_09
特許番号
US04220654

関連ノート

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