Allyl bromide → Ethyl 4-allyloxy-3-methylbenzofuran-2-carboxylate

HRID 978110Notes

Reaction equation

HRID 978110 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([OH:16])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2].[CH2:17](Br)[CH:18]=[CH2:19].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:19]([O:16][C:12]1[C:9]2[C:10]([CH3:11])=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[O:7][C:8]=2[CH:15]=[CH:14][CH:13]=1)[CH:18]=[CH2:17]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 748649Ethyl 4-hydroxy-3-methyl-1-benzofuran-2-carboxylate

Product 1

HCID 13849488Ethyl 4-allyloxy-3-methylbenzofuran-2-carboxylateYield 92.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of ethyl-4-hydroxy-3-methylbenzofuran-2-carboxylate (11.0 g, 50 mmol), allyl bromide (4.8 ml, 55 mmol) and potassium carbonate (55 mmol) was refluxed in acetone (300 ml) for 4 hours. The resulting mixture was cooled, filtered and concentrated. The residue was chromatographed (silica gel, eluted with 5% ethyl acetate in hexane) to give 12 g of the title compound, m.p. 64°-65° C.

Workup

  1. temperatureThe resulting mixture was cooled
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe residue was chromatographed
  5. wash(silica gel, eluted with 5% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-9f06f4d69168453a8e7b43c686f602f6
Source dataset
uspto-grants-1987_05
Patent number
US04663347

Reaction notes

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