HCID 59648645, compound → HCID 59648655, compound

HRID 1363280Notes

Reaction equation

HRID 1363280 reaction equation
[C:1]1([C:7]#[C:8][C:9]2[CH:10]=[C:11]([CH:14]=[O:15])[O:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CO.[Pd]>[CH2:8]([C:9]1[CH:10]=[C:11]([CH:14]=[O:15])[O: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 59648645HCID 59648645, compound

Product 1

HCID 59648655HCID 59648655, compoundYield 97.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-phenylethynyl-furan-2-carbaldehyde (1.54 g, 7.84 mmol) in MeOH was added Pd/C (154 mg, 10% Pd by weight). A vacuum was applied to the reaction mixture and back filled (×4) with H2. The reaction was then allowed to stir at rt for 14 h under an atmosphere of H2 before being filtered through a plug of Celite® with EtOAc. The reaction was then concentrated in vacuo to give 4-phenethyl-furan-2-carbaldehyde as a colorless oil (1.53 g, 97%). 1H NMR (400 MHz, CDCl3) δ ppm 9.59 (d, J=0.6 Hz, 1H) 7.40 (d, J=0.8 Hz, 1H) 7.28-7.34 (m, 2H) 7.20-7.26 (m, 1H) 7.14-7.20 (m, 2H) 7.05 (d, J=0.6 Hz, 1H) 2.87-2.94 (m, 2H) 2.78-2.85 (m, 2H).

Workup

  1. additionback filled (×4) with H2
  2. filtrationbefore being filtered through a plug of Celite® with EtOAc
  3. concentrationThe reaction was then concentrated in vacuo

Sources & evidence

ORD record
ord-d3ee2126a53e4471901c01f70216885e
Source dataset
uspto-grants-2011_02
Patent number
US07884124B2

Reaction notes

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