1-Iodo-2-(methoxymethoxy)benzene → 2-Benzyl-3-hydroxy-6-(2-hydroxyphenyl)pyridine

Participants

Reaction Steps

A mixture of 641 mg of (2-benzyl-3-methoxymethyloxy-6-pyridyl)tributyltin (Production Example 18), 327 mg of 2-methoxymethyloxyiodobenzene (Production Example 20), 71.6 mg of tetrakis(triphenylphosphine)palladium(0) and 7 ml of xylene was heated under refluxed for one hour in nitrogen atmosphere. After cooling as it was, the mixture was filtered through silica gel and the solvent was removed. To the residue was added 2 ml of trifluoroacetic acid, followed by stirring at room temperature overnight. The reaction solution was neutralized by aqueous potassium carbonate. Ethyl acetate was added thereto, and the organic phase was washed with water and brine, dried over anhydrous magnesium sulfate and the solvent was removed. The residue was subjected to silica gel column chromatography using 30% ethyl acetate/hexane, to give 54.5 mg of the target compound.

Provenance & Evidence