HCID 59409719, compound → HCID 59409771, compound

HRID 1892081Notes

Reaction equation

HRID 1892081 reaction equation
[C:1]([C:8]1[CH:9]=[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[S:11][CH:12]=1)#[C:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]>[Pd].CO>[CH2:1]([C:8]1[CH:9]=[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[S:11][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

4

Reactant 1

HCID 59409719HCID 59409719, compound

Product 1

HCID 59409771HCID 59409771, compoundYield 79.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5% Palladium on carbon (2.52 g) was added to a solution of compound 1016 (5.94 g, 23.7 mmol) in methanol (100 mL). The reaction mixture was stirred under a hydrogen atmosphere (1 atm) for 12 hours. The reaction mixture was filtered through celite and the clear solution was concentrated under vacuum to give ethyl 4-heptylthiophene-2-carboxylate (1017, 4.80 g) which was directly used in the next step without further purification. Rf=0.78 (10% EtOAc in Hexane).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe clear solution was concentrated under vacuum

Sources & evidence

ORD record
ord-a738f417c71c4e82b8a583aec039b4da
Source dataset
uspto-grants-2013_08
Patent number
US08507647B2

Reaction notes

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