Tetrahydrofuran → {4-Ethyl-5-[5-(3-fluoro-4-phenoxyphenyl)-1,2,4-oxadiazol-3-yl]-2-thienyl}methanol

Participants

Reaction Steps

The crude product of the title compound was synthesized by conducting the similar reaction to that mentioned in Example 12 (12a) using 3-fluoro-4-phenoxybenzoic acid (0.12 g, 0.50 mmol) that was obtained in Example 11 (11e), 1-hydroxybenzotriazole (72 mg, 0.53 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.10 g, 0.53 mmol), 5-({[t-butyl(dimethyl)silyl]oxy}methyl)-3-ethyl-N′-hydroxythiophene-2-carboximidamide (0.15 g, 0.48 mmol) that was obtained in Example 10 (10d), and a 1.0 M solution of tetrabutylammonium fluoride in tetrahydrofuran (0.96 ml, 0.96 mmol). Subsequently, the crude product of the title compound thus obtained was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (1:3) as the eluent to afford the title compound (0.16 g) in a yield of 85% as a pale yellowish crystalline solid.

Provenance & Evidence