HCID 14579780, compound → HCID 15029659, compound

HRID 1607250Notes

Reaction equation

HRID 1607250 reaction equation
[CH3:1][O:2][C:3]1[CH:31]=[CH:30][C:6]([C:7]([C:9]2[O:10][C:11]3[C:18]([CH2:19][CH2:20][CH3:21])=[C:17]([O:22]CC4C=CC=CC=4)[CH:16]=[CH:15][C:12]=3[C:13]=2[CH3:14])=O)=[CH:5][CH:4]=1>C(O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][C:9]2[O:10][C:11]3[C:18]([CH2:19][CH2:20][CH3:21])=[C:17]([OH:22])[CH:16]=[CH:15][C:12]=3[C:13]=2[CH3:14])=[CH:30][CH:31]=1

Participants

4

Reactant 1

HCID 14579780HCID 14579780, compound

Product 1

HCID 15029659HCID 15029659, compoundYield 14.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-(p-methoxybenzoyl)-3-methyl-6-benzyloxy-7-propylbenzofuran (1.04 gm, 2.5 mmoles) in ethanol (100 mL) was hydrogenated in a Parr hydrogenator in the presence of 10% palladium on charcoal for a period of 24 hours. The catalyst was filtered off and the filtrate was concentrated in vacuo. The residue was purified by chromatography on silica gel and eluted with 25% ethylacetate in hexane to yield 110 mg of 2-(p-methoxybenzyl)-3-methyl-6-hydroxy-7-propylbenzofuran.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by chromatography on silica gel
  4. washeluted with 25% ethylacetate in hexane

Sources & evidence

ORD record
ord-dc77dd4549044734bbbe6b2bd56630db
Source dataset
uspto-grants-1989_09
Patent number
US04863958

Reaction notes

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