4-Methoxyphenol → HCID 20065062, compound

HRID 359476Notes

Reaction equation

HRID 359476 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1.[H-].[Na+]>CN(C)C=O>[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][C:2]2[C:7]([C:8]#[N:9])=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 90154-MethoxyphenolHCID 24758Sodium hydrideHCID 810792-Chloronicotinonitrile

Product 1

HCID 20065062HCID 20065062, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Chloro-3-cyanopyridine is reacted with 4-methoxyphenol in the presence of sodium hydride in dimethylformamide to give 2-(4-methoxyphenoxy)-3-cyanopyridine, which is subjected to Grignard reaction with 2-bromothiophene in a mixed solvent of ether and benzene, followed by treatment with hydrochloric acid to give 2-(4-methoxyphenoxy)-3-(2-thenoyl)pyridine. The thus obtained compound is subjected to demethylation reaction with the use of aluminium chloride and 1-butanethiol in dichloromethane to give 2-(4-hydroxyphenoxy)-3-(2-thenoyl)pyridine.

Sources & evidence

ORD record
ord-8fe8c7cef6e445259cb3be9571f3cb85
Source dataset
uspto-grants-1991_03
Patent number
US05001137

Reaction notes

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