5-(2-Methoxycarbonyl-vinyl)-thiophene-2-carboxylic acid → 5-(2-Methoxycarbonyl-ethyl)-thiophene-2-carboxylic acid

HRID 431500Notes

Reaction equation

HRID 431500 reaction equation
[CH3:1][O:2][C:3]([CH:5]=[CH:6][C:7]1[S:11][C:10]([C:12]([OH:14])=[O:13])=[CH:9][CH:8]=1)=[O:4]>CO.[Pd]>[CH3:1][O:2][C:3]([CH2:5][CH2:6][C:7]1[S:11][C:10]([C:12]([OH:14])=[O:13])=[CH:9][CH:8]=1)=[O:4]

Participants

4

Reactant 1

HCID 542089615-(2-Methoxycarbonyl-vinyl)-thiophene-2-carboxylic acid

Product 1

HCID 108676335-(2-Methoxycarbonyl-ethyl)-thiophene-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2.37 g (11.18 mmol) of 5-(2-methoxycarbonyl-vinyl)-thiophene-2-carboxylic acid were dissolved in 170 ml of methanol. After addition of 500 mg of 10% palladium on charcoal (Degussa E 101 R/D 10%) the mixture was hydrogenated for 7 hours at atmospheric pressure (approx. 1 bar) and room temperature. After filtration and evaporation the yield of the title compound was 2.4 g (purity>99% (HPLC)).

Workup

  1. filtrationAfter filtration and evaporation the yield of the title compound

Sources & evidence

ORD record
ord-a687f507f94645a0a8515b24d9c7d895
Source dataset
uspto-grants-2003_12
Patent number
US06660728B2

Reaction notes

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