Ethyl Acetate → HCID 12616263, compound

HRID 1837686Notes

Reaction equation

HRID 1837686 reaction equation
Br[C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH:7]=[O:8].[CH3:9][S-:10].[Na+].C(OCC)(=O)C>CN(C)C=O>[CH3:9][S:10][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[CH:7]=[O:8]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 27970793-Bromothiophene-2-carboxaldehydeHCID 4378561Sodium methanethiolate

Product 1

HCID 12616263HCID 12616263, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.44 g of 3-bromo-2-thiophenecarboxaldehyde and 1.63 g of sodium thiomethoxide were dissolved in 20 ml of N,N-dimethylformamide, and the mixture was stirred for 3 hours under ice-cooling. Ethyl acetate was added to the reaction solution. The mixture was washed with water and brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the resulting crude product was purified by silica gel column chromatography (ethyl acetate:hexane=1:9), to give 3.36 g of the title compound as a yellow oil.

Workup

  1. temperaturecooling
  2. washThe mixture was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe resulting crude product was purified by silica gel column chromatography (ethyl acetate:hexane=1:9)

Sources & evidence

ORD record
ord-7b0cf485b37e4bb49b6490e9b001c07d
Source dataset
uspto-grants-2004_08
Patent number
US06784192B2

Reaction notes

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