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

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.

1. customthe solvent was evaporated
2. temperatureto cool to room temperature
3. additionThe reaction mixture was diluted with water (100 mL)
4. stirringstirred for 10 min
5. extractionfollowed by extraction with ethyl acetate (3×50 mL)
6. washThe combined organic layers were washed with water (2×50 mL) and brine (50 mL)
7. customThe organic phase obtained
8. dry with materialwas dried over anhydrous sodium sulfate
9. concentrationconcentrated
10. customto obtain a crude product, which
11. customwas purified by column chromatography (silica gel, 1.0% methanol in chloroform)

ORD record

ord-4fb7ea95b9d247feadc696d36efd3b05

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08629277B2