Allyl bromide → HCID 19910750, compound

HRID 1607279Notes

Reaction equation

HRID 1607279 reaction equation
[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]([CH2:7][CH2:8][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])=[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]([CH2:7][CH2:8][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])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 14579796HCID 14579796, compound

Product 1

HCID 19910750HCID 19910750, compoundYield 60.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-(p-methoxyphenethyl)-3-methyl-4-hydroxybenzofuran (1.3 gm; 4.6 mmoles), potassium carbonate (1.38 gm, 10 mmoles), and allyl bromide (1.2 gm, 10 mmoles) in acetone (50 mL) was refluxed for a period of 5 hours. The solids were filtered off and the filtrate was concentrated in vacuo. The residue was chromatographed on silica gel and eluted with 15% ethylacetate in hexane to yield 0.9 gm of 2-(p-methoxyphenethyl)-3-methyl-4-allyloxybenzofuran, which was used as such for the next step.

Workup

  1. temperaturewas refluxed for a period of 5 hours
  2. filtrationThe solids were filtered off
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was chromatographed on silica gel
  5. washeluted with 15% ethylacetate in hexane

Sources & evidence

ORD record
ord-722cbc3c7c9b4c4fbf94b7686219547e
Source dataset
uspto-grants-1989_09
Patent number
US04863958

Reaction notes

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