Ethyl bromoacetate → HCID 86629327, compound

HRID 549920Notes

Reaction equation

HRID 549920 reaction equation
[OH:1][C:2]1[C:10]2[CH:9]=[CH:8][O:7][C:6]=2[C:5]([O:11][CH3:12])=[CH:4][CH:3]=1.Br[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH3:12][O:11][C:5]1[C:6]2[O:7][CH:8]=[CH:9][C:10]=2[C:2]([O:1][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 19261745HCID 19261745, compound

Product 1

HCID 86629327HCID 86629327, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 4-hydroxy-7-methoxybenzo[b]furan (2.0 g, 12.2 mmol; prepared according to Eur. J. Med. Chem. 1981, 16, 563), ethyl bromoacetate (2.2 g, 13.2 mmol), potassium carbonate (2.0 g, 14.5 mmol) and 2-butanone (50 mL) was refluxed for 10 h, then filtered and evaporated in vacuo. The residue was purified by column chromatography (silica gel Fluka 60, chloroform) affording ethyl (7-methoxybenzo[b]furan-4-yloxy)acetate.

Workup

  1. temperaturewas refluxed for 10 h
  2. filtrationfiltered
  3. customevaporated in vacuo
  4. customThe residue was purified by column chromatography (silica gel Fluka 60, chloroform)

Sources & evidence

ORD record
ord-8160c3e0726347a787a3109bb27b8c27
Source dataset
uspto-grants-2011_05
Patent number
US07943613B2

Reaction notes

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