Phase-transfer catalyzed alkoxylation of 2-(dichloromethyl) furan by alcohols in the presence of potassium hydroxide

Reaction of 2-(dichloromethyl)furan (I) with KOH in a CH₂Cl₂ medium and in the presence of alcohols (methanol, ethanol, and n-butanol) and a catalytic amount of triethylbenzylammonium chloride (TEBAC) results in the formation of 2-chloro-methylene-5-alkoxy-2, 5-dihydrofurans (II) (mixtures of Z- and E-isomers) and 2-dialkoxymethylfurans (III), in overall yields of up to 96%. Reaction with isopropyl and tert-butyl alcohols gave only the corresponding products (II), in 21 and 12% yield, respectively.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 6, pp. 1403–1407, June, 1991.