Catechol → HCID 10655488, compound

Participants

Reaction Steps

Catechol (55 g) was dissolved in a methanol solution of sodium methoxide prepared from metallic sodium (11.5 g). Methyl 2-chloropropionate (62 g) was added thereto and refluxed. Extraction with ether and purification on a silica gel column afforded 15 g of methyl 2-(2-hydroxyphenoxy)propionate. This product and 3,4-dichlorobenzylcyanide were dissolved in an ethanol solution of sodium ethoxide prepared from metallic sodium (7 g), and the mixture was refluxed with heat for 3 hours. Extraction with ether and purification on a silica gel column afforded 3 g of 2-(3,4-dichlorophenyl)-4-(2-hydroxyphenyl)-3-oxopentanonitrile. This compound (1 g), 2,3-dichloro-5-trifluoromethylpyridine (0.6 g), and potassium carbonate (0.4 g) were dissolved in dimethylformamide, and the mixture was stirred for 2 hours at 120° C. Extraction with ether and purification on a silica gel column afforded 0.6 g of 4-[2-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenoxy]-2-(3,4-dichlorophenyl)-3-oxopentanonitrile (Compound 18).

Provenance & Evidence