Pyridine → 2-(3-Methoxy-phenyl)-7-benzofurancarbaldehye

HRID 1646965Notes

Reaction equation

HRID 1646965 reaction equation
[OH:1][C:2]1[C:9](I)=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH3:11][O:12][C:13]1[CH:14]=[C:15]([C:19]#[CH:20])[CH:16]=[CH:17][CH:18]=1.N1C=CC=CC=1>C(OCC)(=O)C>[CH3:11][O:12][C:13]1[CH:14]=[C:15]([C:19]2[O:1][C:2]3[C:3]([CH:4]=[O:5])=[CH:6][CH:7]=[CH:8][C:9]=3[CH:20]=2)[CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6407531-Ethynyl-3-methoxybenzeneHCID 152099202-Hydroxy-3-iodobenzaldehyde

Product 1

HCID 149956822-(3-Methoxy-phenyl)-7-benzofurancarbaldehyeYield 143%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 11 g of 2-hydroxy-3-iodo benzaldehyde, 8.6 g of (3-methoxy-phenyl) acetylene and 150 ml of pyridine was refluxed for 45 minutes and then allowed to return to ambient temperature. Ethyl acetate was added, and washing was carried out with an acid solution, followed by drying and concentrating to obtain 16 g of product which was chromatographed on silica (eluant: hexane-isopropyl ether (7-3)) to obtain 9 g of the desired product melting at 55° C. to 60° C.

Workup

  1. temperaturewas refluxed for 45 minutes
  2. customto return to ambient temperature
  3. washwashing
  4. customby drying
  5. concentrationconcentrating

Sources & evidence

ORD record
ord-407160e13ca745139678545078a93ff1
Source dataset
uspto-grants-1993_01
Patent number
US05182295

Reaction notes

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