HCID 14579787, compound → HCID 14579788, compound

HRID 1534231Notes

Reaction equation

HRID 1534231 reaction equation
[CH3:1][O:2][C:3]1[CH:32]=[CH:31][C:6]([C:7]([C:9]2[O:10][C:11]3[CH:18]=[CH:17][C:16]([O:19]CC(C4C=CC(OC)=CC=4)=O)=[CH:15][C:12]=3[C:13]=2[CH3:14])=O)=[CH:5][CH:4]=1>C(O)(=O)C.[Zn]>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][C:9]2[O:10][C:11]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][C:12]=3[C:13]=2[CH3:14])=[CH:31][CH:32]=1

Participants

4

Reactant 1

HCID 14579787HCID 14579787, compound

Product 1

HCID 14579788HCID 14579788, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 2-(p-methoxybenzoyl)-3-methyl-5-(p-methoxyphenacyloxy)-benzofuran (5.35 gm, 12.4 mmoles) and zinc dust (5.3 gm) in acetic acid (200 mL) was stirred at room temperature overnight. The solids were filtered off and washed with some ethylacetate. The filtrate was concentrated in vacuo and the residue was chromatographed on silica gel using 20% ethylacetate in hexane as eluent to yield 0.85 gm (26%) of 2-(p-methoxybenzyl)-3-methyl-5-hydroxybenzofuran, mp. 128°-131° C.

Workup

  1. filtrationThe solids were filtered off
  2. washwashed with some ethylacetate
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was chromatographed on silica gel using 20% ethylacetate in hexane as eluent

Sources & evidence

ORD record
ord-4ec1282c6d0346fc8aa82c8e127bfee8
Source dataset
uspto-grants-1992_02
Patent number
US05087638

Reaction notes

Loading…