HCID 67486354, compound → HCID 67486720, compound

HRID 2371260Notes

Reaction equation

HRID 2371260 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7](/[CH:10]=[C:11](\[C:15]2[CH:20]=[CH:19][C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:17][CH:16]=2)/[C:12]([OH:14])=[O:13])=[CH:8][CH:9]=1)=[O:4].[H][H]>C1COCC1.[Pd]>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH2:10][CH:11]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:17][CH:16]=2)[C:12]([OH:14])=[O:13])=[CH:8][CH:9]=1)=[O:4]

Participants

5

Reactant 2

HCID 67486354HCID 67486354, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67486720HCID 67486720, compoundYield 81.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To 5-[(E)-2-(4-tert-Butyl-phenyl)-2-carboxy-vinyl]-thiophene-2-carboxylic acid methyl ester (600 mg, 1.7 mmol) in 50 ml THF and 10 ml 1 NHCl was added 10% palladium on carbon (1.5 g). The resulting mixture was stirred under 50 psi hydrogen gas for 2 hours. The catalyst was filtered off and the solvent was evaporated. The residue was sonicated in hexane for 30 seconds. The solvent was filtered to afford 5-[2-(4-tert-Butyl-phenyl)-2-carboxy-ethyl]-thiophene-2-carboxylic acid methyl ester as a yellow solid (480 mg, 81%).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent was evaporated
  3. customThe residue was sonicated in hexane for 30 seconds
  4. filtrationThe solvent was filtered

Sources & evidence

ORD record
ord-b348baedb73e4ae3b104f5f508e524d7
Source dataset
uspto-grants-2014_04
Patent number
US08710236B2

Reaction notes

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