Methanol → 2-[3-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]pentanoic Acid

Participants

Reaction Steps

2.1 I of 1N sodium hydroxide solution are added to a solution of 347 g (1.14 mol) of ethyl 2-[3-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]-pentanoate in 1.4 I of methanol, and the mixture is stirred at room temperature for 24 hours. The reaction mixture is diluted with 1 I of water and extracted twice with 1 I of tert-butyl methyl ether each time. The aqueous phase is acidified to a pH of 2 using concentrated hydrochloric acid and extracted twice with 2 I of tert-butyl methyl ether each time. The combined organic phases are evaporated, and the residue is recrystallised from 100 ml of toluene: 2-[3-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]pentanoic acid is obtained as colourless crystals of m.p. 98-100°.

Provenance & Evidence