Ethyl bromoacetate → HCID 14570913, compound

HRID 1607285Notes

Reaction equation

HRID 1607285 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-b7aaf4b661c345fd91e236f91d483345
Source dataset
uspto-grants-1989_09
Patent number
US04863958

Reaction notes

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