Allyl bromide → 2-(p-Methoxybenzoyl)-3-methyl-4-allyloxybenzofuran

HRID 1607273Notes

Reaction equation

HRID 1607273 reaction equation
[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]([C:7]([C:9]2[O:10][C:11]3[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[C:12]=3[C:13]=2[CH3:14])=[O:8])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:28](Br)[CH:29]=[CH2:30]>CC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([C:9]2[O:10][C:11]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH2:30][CH:29]=[CH2:28])[C:12]=3[C:13]=2[CH3:14])=[O:8])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 145797912-(p-Methoxybenzoyl)-3-methyl-4-hydroxybenzofuran

Product 1

HCID 150296682-(p-Methoxybenzoyl)-3-methyl-4-allyloxybenzofuran

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-(p-methoxybenzoyl)-3-methyl-4-hydroxybenzofuran (0.60 gm; 2.2 mmoles), potassium carbonate (0.83 gm; 6.0 mmoles) and allyl bromide (0.73 gm; 6.0 mmoles) in acetone (25 mL) was refluxed for a period of 22 hours. The reaction mixture was cooled, filtered through Celite, and concentrated in vacuo. The residue was chromatographed on silica gel using 15% ethylacetate in hexane as eluent to yield 2-(p-methoxybenzoyl)-3-methyl-4-allyloxybenzofuran.

Workup

  1. temperaturewas refluxed for a period of 22 hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationfiltered through Celite
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica gel using 15% ethylacetate in hexane as eluent

Sources & evidence

ORD record
ord-d4cbadfd5a6e414e943a3b047199d3b1
Source dataset
uspto-grants-1989_09
Patent number
US04863958

Reaction notes

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