HCID 14579776, compound → HCID 14579777, compound

HRID 1607245Notes

Reaction equation

HRID 1607245 reaction equation
[F:1][C:2]1[CH:23]=[CH:22][C:5]([C:6]([C:8]2[O:9][C:10]3[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([CH2:19][CH:20]=[CH2:21])[C:11]=3[C:12]=2[CH3:13])=O)=[CH:4][CH:3]=1>C(O)C.[Pd]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:8]2[O:9][C:10]3[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([CH2:19][CH2:20][CH3:21])[C:11]=3[C:12]=2[CH3:13])=[CH:22][CH:23]=1

Participants

4

Reactant 1

HCID 14579776HCID 14579776, compound

Product 1

HCID 14579777HCID 14579777, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-(p-fluorobenzoyl)-3-methyl-4-allyl-5-hydroxybenzofuran (1.5 gm; 4.8mmoles) in ethanol (50 mL) was hydrogenated in a Parr apparatus in presence of 10% palladium on carbon. The catalyst was removed by filtration and the filtrate was concentrated to dryness. The residue was chromatographed on silica gel using 20% ethylacetate in hexane as eluent to yield 600 mg (42%) of 2-(p-fluorobenzyl)-3-methyl-4-propyl-5-hydroxybenzofuran, mp 121°-123° C.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated to dryness
  3. customThe residue was chromatographed on silica gel using 20% ethylacetate in hexane as eluent

Sources & evidence

ORD record
ord-9770bd7dbc0e41a191ea563b5b7ec7a6
Source dataset
uspto-grants-1989_09
Patent number
US04863958

Reaction notes

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