Ethyl Acetate → 7-(2-Methoxycarbonylvinyl)imidazo[5,1-b]thiazole

HRID 1839314Notes

Reaction equation

HRID 1839314 reaction equation
C1(P(=[CH:20][C:21]([O:23][CH3:24])=[O:22])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH:25]([C:27]1[N:28]=[CH:29][N:30]2[CH:34]=[CH:33][S:32][C:31]=12)=O.C(OCC)(=O)C>CO>[CH3:24][O:23][C:21]([CH:20]=[CH:25][C:27]1[N:28]=[CH:29][N:30]2[CH:34]=[CH:33][S:32][C:31]=12)=[O:22]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 22390357Imidazo(4,3-b)(1,3)thiazole-7-carbaldehyde

Product 1

HCID 699303387-(2-Methoxycarbonylvinyl)imidazo[5,1-b]thiazoleYield 111.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl triphenylphosphoranylideneacetate (500 mg) was added to a solution of 150 mg of 7-formylimidazo[5,1-b]thiazole in 15 ml of methanol. The mixture was stirred at room temperature for 15 min. Ethyl acetate was added thereto. The mixture was washed with water, dried over anhydrous magnesium sulfate, and filtered. The solvent was removed by distillation under the reduced pressure. The residue was purified by column chromatography on silica gel(chloroform:methanol=20:1) to give 228 mg of 7-(2-methoxycarbonylvinyl)imidazo[5,1-b]thiazole (a mixture of geometrical isomers).

Workup

  1. washThe mixture was washed with water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customThe solvent was removed by distillation under the reduced pressure
  5. customThe residue was purified by column chromatography on silica gel(chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-d815241a42714717b1e47ce8b7cd943f
Source dataset
uspto-grants-2004_01
Patent number
US06677331B2

Reaction notes

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