tert-butyl (2E)-3-(3-formyl-2-thienyl)acrylate → Tert-butyl 3-(3-formyl-2-thienyl)propanoate

HRID 64431Notes

Reaction equation

HRID 64431 reaction equation
[CH:1]([C:3]1[CH:7]=[CH:6][S:5][C:4]=1/[CH:8]=[CH:9]/[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:2]>CO.[C].[Pd]>[CH:1]([C:3]1[CH:7]=[CH:6][S:5][C:4]=1[CH2:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:2]

Participants

4

Reactant 1

HCID 86713442tert-butyl (2E)-3-(3-formyl-2-thienyl)acrylate

Product 1

HCID 86713443Tert-butyl 3-(3-formyl-2-thienyl)propanoateYield 80.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 650 mg of tert-butyl (2E)-3-(3-formyl-2-thienyl)acrylate in 15 ml of methanol was added 150 mg of 10% palladium-carbon, followed by stirring for 5 hours under a hydrogen atmosphere. After filtration through Celite, the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 530 mg of tert-butyl 3-(3-formyl-2-thienyl)propanoate.

Workup

  1. filtrationAfter filtration through Celite
  2. customthe solvent was evaporated under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-30cb8611e6d643ee88b6b3d6e636b36b
Source dataset
uspto-grants-2016_09
Patent number
US09447090B2

Reaction notes

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