Ethyl bromoacetate → HCID 14570913, compound

HRID 1534253Notes

Reaction equation

HRID 1534253 reaction equation
[OH:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][C:7]2[O:8][C:9]3[C:16]([Cl:17])=[CH:15][C:14]([CH2:18][CH2:19][CH3:20])=[C:13]([O:21][C:22](=[O:24])[CH3:23])[C:10]=3[C:11]=2[CH3:12])=[CH:4][CH:3]=1.[CH2:27]([O:29][C:30](=[O:33])[CH2:31]Br)[CH3:28].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:30]([CH2:31][O:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][C:7]2[O:8][C:9]3[C:16]([Cl:17])=[CH:15][C:14]([CH2:18][CH2:19][CH3:20])=[C:13]([O:21][C:22](=[O:24])[CH3:23])[C:10]=3[C:11]=2[CH3:12])=[CH:4][CH:3]=1)([O:29][CH2:27][CH3:28])=[O:33]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 14570912HCID 14570912, compound

Product 1

HCID 14570913HCID 14570913, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-(p-hydroxybenzyl)-3-methyl-4-acetoxy-5-propyl-7-chlorobenzofuran (107 mg; 0.28 mmole), ethylbromoacetate (100 mg, 0.60 mmole), potassium carbonate (100 mg, 0.73 mmole) in acetone (10 mL) was refluxed for 30 minutes. The solids were filtered off, the filtrate was concentrated in vacuo to yield a residue that was purified by chromatography on silica gel. Elution with 20% ethylacetate in hexane yielded 133 (100%) of 2-(p-carboethoxymethoxybenzyl)-3-methyl-4-acetoxy-5-propyl-7-chlorobenzofuran.

Workup

  1. temperaturewas refluxed for 30 minutes
  2. filtrationThe solids were filtered off
  3. concentrationthe filtrate was concentrated in vacuo
  4. customto yield a residue that
  5. customwas purified by chromatography on silica gel
  6. washElution with 20% ethylacetate in hexane

Sources & evidence

ORD record
ord-fe174cb4fddd44edbe14b36f0f644808
Source dataset
uspto-grants-1992_02
Patent number
US05087638

Reaction notes

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