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

HRID 27181

Reaction equation

HRID 27181 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

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.).

Workup

  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

Sources & evidence

ORD record
ord-43635b8c0f004ae4ab0630f6b70e2e18
Source dataset
uspto-grants-1980_09
Patent number
US04220654

Linked notes

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