3-[5-Hydroxy-2-(4-hydroxy-phenyl)-benzofuran-7-yl]-acrylonitrile → 3-[5-Hydroxy-2-(4-hydroxy-phenyl)-benzofuran-7-yl]-propionitrile

HRID 1836003Notes

Reaction equation

HRID 1836003 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]#[N:21])[C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=3)=[CH:7][C:6]=2[CH:17]=1>CO.[Pd]>[OH:1][C:2]1[CH:3]=[C:4]([CH2:18][CH2:19][C:20]#[N:21])[C:5]2[O:9][C:8]([C:10]3[CH:11]=[CH:12][C:13]([OH:16])=[CH:14][CH:15]=3)=[CH:7][C:6]=2[CH:17]=1

Participants

4

Reactant 1

HCID 688406933-[5-Hydroxy-2-(4-hydroxy-phenyl)-benzofuran-7-yl]-acrylonitrile

Product 1

HCID 101493813-[5-Hydroxy-2-(4-hydroxy-phenyl)-benzofuran-7-yl]-propionitrileYield 25.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 3-[5-hydroxy-2-(4-hydroxy-phenyl)-benzofuran-7-yl]-acrylonitrile 64 (0.028 g, 0.1 mmol) in methanol (1 mL) was purged with nitrogen and 10% palladium on carbon added. The reaction vessel was evacuated and a hydrogen balloon added. After an hour, the reaction was filtered and the solvent removed in vacuo. The product was purified via flash chromatography, eluting with 3% methanol in dichloromethane to give 0.007 g of 3-[5-hydroxy-2-(4-hydroxy-phenyl)-benzofuran-7-yl]-propionitrile 65: 1H NMR (DMSO-d6) δ 9.84 (s, 1 H), 9.17 (s, 1 H), 7.73 (d, 2 H, J=8.6 Hz), 7.02 (s, 1 H), 6.87 (d, 2 H, J=8.6 Hz), 6.79 (d, 1 H, J=2.3 Hz), 6.62 (d, 1 H, J=2.2 Hz), 3.12 (t, 2 H, J=7.1 Hz), 2.96 (t, 2 H, J=7.4 Hz); MS 280 (M+H)+.

Workup

  1. additionadded
  2. customThe reaction vessel was evacuated
  3. additiona hydrogen balloon added
  4. waitAfter an hour
  5. filtrationthe reaction was filtered
  6. customthe solvent removed in vacuo
  7. customThe product was purified via flash chromatography
  8. washeluting with 3% methanol in dichloromethane

Sources & evidence

ORD record
ord-5a46c5b6aa434a9f94db15a3320adc73
Source dataset
uspto-grants-2004_08
Patent number
US06774248B2

Reaction notes

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