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

Temperature

5 °C

3-Benzyl-5-{2-[3,4-bis-(tert-butyl-dimethyl-silanyloxy)-phenyl]-vinyl}-[1,2,4]oxadiazole (compound of Example 4, Method B, Step 1) (4.60 g, 8.79 mmol) was dissolved in THF (30 mL) and cooled to 5° C. This was followed by addition of 1 M solution of TBAF in THF (12.72 mL, 43.95 mL) over a period of 15 min and allowed to warm to room temperature. After 3 h stirring at room temperature, the solvent was evaporated and the reaction mixture was allowed to cool to room temperature. The reaction mixture was diluted with water (30 mL) and stirred for 10 min followed by extraction with ethyl acetate (3×20 mL). The combined organic layers were washed with water (2×10 mL) and brine (10 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, 0.5% methanol in chloroform) to afford the title compound.

1. temperatureto warm to room temperature
2. customthe solvent was evaporated
3. temperatureto cool to room temperature
4. additionThe reaction mixture was diluted with water (30 mL)
5. stirringstirred for 10 min
6. extractionfollowed by extraction with ethyl acetate (3×20 mL)
7. washThe combined organic layers were washed with water (2×10 mL) and brine (10 mL)
8. customThe organic phase obtained
9. dry with materialwas dried over anhydrous sodium sulfate
10. concentrationconcentrated
11. customto obtain a crude product, which
12. customwas purified by column chromatography (silica gel, 0.5% methanol in chloroform)

ORD record

ord-2dee1e238c644c00b4ba7471cd03ec4e

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08629277B2