4-(2-Phenyleth-1-ynyl)thiophene-2-carbaldehyde → 4-Phenethylthiophene-2-carbaldehyde

HRID 1363251Notes

Reaction equation

HRID 1363251 reaction equation
[C:1]1([C:7]#[C:8][C:9]2[CH:10]=[C:11]([CH:14]=[O:15])[S:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>[Pd].CCOC(C)=O>[CH2:8]([C:9]1[CH:10]=[C:11]([CH:14]=[O:15])[S:12][CH:13]=1)[CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 27371394-(2-Phenyleth-1-ynyl)thiophene-2-carbaldehyde

Product 1

HCID 235874144-Phenethylthiophene-2-carbaldehydeYield 95.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Under a N2 atmosphere, 4-(phenylethynyl)thiophene-2-carbaldehyde (386 mg, 1.8 mmol) was dissolved EtOAc (6 mL), and palladium on carbon (Pd/C) (44 mg) was added. The flask was evacuated and flushed with H2 (3×). The reaction stirred at rt overnight with a balloon of H2. The mixture was filtered through a plug of Celite® and the filtrate was concentrated to give 4-phenethylthiophene-2-carbaldehyde (373 mg, 95%). 1H NMR (400 MHz, CDCl3) δ (ppm): 9.87 (d, 1H), 7.56 (d, 1H), 7.33 (m, 1H), 7.29 (m, 2H), 7.23 (m, 1H), 7.16 (m, 2H), 2.97 (m, 4H).

Workup

  1. additionwas added
  2. customThe flask was evacuated
  3. customflushed with H2 (3×)
  4. filtrationThe mixture was filtered through a plug of Celite®
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-cd124b631b23419b97c113dd1fcdac57
Source dataset
uspto-grants-2011_02
Patent number
US07884124B2

Reaction notes

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