HCID 14579787, compound → HCID 14579788, compound

HRID 1607264Notes

Reaction equation

HRID 1607264 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-methyl5-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-043c5dca5b1240939741ddad6eaeedb9
Source dataset
uspto-grants-1989_09
Patent number
US04863958

Reaction notes

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