Tetrabutylammonium Fluoride → 4-[2-(3-Propyl-1,2,4-oxadiazol-5-yl)ethenyl]benzene-1,2-diol

Participants

Reaction Steps

5-{2-[3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-vinyl}-3-propyl-[1,2,4]oxadiazole (compound of Example 3, Method B, Step 1; 38 g, 80.03 mmol) was dissolved in THF (300 mL) followed by addition of 1 M solution of TBAF in THF (139 mL, 480.18 mmol) over a period of 10 min. After stirring at room temperature for 3 h, the solvent was evaporated and the reaction mixture was allowed to cool to room temperature. The reaction mixture was diluted with water (100 mL) and stirred for 10 min followed by extraction with ethyl acetate (3×50 mL). The combined organic layers were washed with water (2×50 mL) and brine (50 mL). The organic phase obtained was dried over anhydrous sodium sulfate and concentrated to obtain a crude product, which was purified by column chromatography (silica gel, 1.0% methanol in chloroform) to afford the title compound.

Provenance & Evidence