1-(4-Hydroxy-benzofuran-5-yl)-ethanone → HCID 58762705, compound

HRID 858659Notes

Reaction equation

HRID 858659 reaction equation
[OH:1][C:2]1[C:7]2[CH:8]=[CH:9][O:10][C:6]=2[CH:5]=[CH:4][C:3]=1[C:11](=O)[CH3:12]>CO.[Pd]>[CH2:11]([C:3]1[C:2]([OH:1])=[C:7]2[CH2:8][CH2:9][O:10][C:6]2=[CH:5][CH:4]=1)[CH3:12]

Participants

4

Reactant 1

HCID 117885801-(4-Hydroxy-benzofuran-5-yl)-ethanone

Product 1

HCID 58762705HCID 58762705, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-(4-Hydroxy-benzofuran-5-yl)-ethanone (1.37 g, 7.8 mmol) and 10 wt % Pd/C (0.7 g, Degussa type) in MeOH (20 mL) was stirred under a balloon of H2 for 24 hours. The reaction mixture was filtered through a pad of celite washing with EtOAc. The filtrate was concentrated to an oil (0.9 g, 70%). 1H NMR (400 MHz, CDCl3): δ 1.21 (t, J=7.6 Hz, 3 H), 2.56 (q, J=7.6 Hz, 2 H), 3.14 (t, J=8.6 Hz, 2 H), 4.59 (t, J=8.6 Hz, 2 H), 4.68 (s, 1H), 6.37 (d, J=8.1 Hz, 1 H), 6.37 (d, J=8.1 Hz, 1 H).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. washwashing with EtOAc
  3. concentrationThe filtrate was concentrated to an oil (0.9 g, 70%)

Sources & evidence

ORD record
ord-21b110b31d3542208fffd39837172783
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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