Sodium Hydroxide → HCID 67398366, compound

5-[2-(4-Methoxy-3-nitro-phenyl)-vinyl]-3-propyl-[1,2,4]oxadiazole (compound of Example 7; 0.140 g, 0.48 mmol) was dissolved in ethyl acetate (10 mL) to which stannous chloride (0.43 g, 1.93 mmol) was added and the reaction mixture was stirred at room temperature. After 8 h, additional stannous chloride (0.32 g, 1.44 mmol) was added and the reaction mixture was stirred at room temperature for about 16-18 h. The pH of the reaction mixture was adjusted to 11 by addition of 10% sodium hydroxide and extracted with ethyl acetate (2×5 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. additionwas added
2. stirringthe reaction mixture was stirred at room temperature for about 16-18 h
3. extractionextracted with ethyl acetate (2×5 mL)
4. washThe combined organic layers were washed with water (2×10 mL) and brine (10 mL)
5. customThe organic phase obtained
6. dry with materialwas dried over anhydrous sodium sulfate
7. concentrationconcentrated
8. customto obtain a crude product, which
9. customwas purified by column chromatography (silica gel, 0.5% methanol in chloroform)

ORD record

ord-167701ddf7be488b919c6ae81125adb7

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08629277B2