Benzonitrile → HCID 19382361, compound

Temperature

-10 °C

Lithium diisopropyl amide (276 mL, 0.4 mol of a 1.5M cyclohexane solution) was added dropwise over 45 minutes under nitrogen atmosphere at -78° C. to -55° C. to a stirred solution of 3-furoic acid (22.4 g, 0.2 mol) in tetrahydrofuran (70 mL). After one hour, the temperature was raised to -10° C. for 1/2 hour. The yellow solution was recooled to -78° C. and benzonitrile (20.6 g, 0.2 mol) was added over 1/4 hour. After one hour at -78° C., the temperature was brought to 0° C. over 21/2 hours. Following a one hour period at 0° C., the reaction was diluted with cold water (200 mL). The tetrahydrofuran was removed in vacuo. The residue was acidified with hydrochloric acid to pH 5 and was left at room temperature over night. The x s mixture was further acidified to pH 3 and the precipitated tan solid was extracted into ether (600 mL). The ether extract was washed with saturated NaCl solution, dried over Na2SO4, filtered and concentrated in vacuo. The product (26.0 g) was recrystallized from n-butyl chloride (100mL) and petroleum ether (100 mL). Weight of light tan solid recovered was 20.5 g.

1. customwas recooled to -78° C.
2. waitAfter one hour at -78° C.
3. customwas brought to 0° C. over 21
4. custom2 hours
5. waitFollowing a one hour period at 0° C.
6. customThe tetrahydrofuran was removed in vacuo
7. waitwas left at room temperature over night
8. extractionthe precipitated tan solid was extracted into ether (600 mL)
9. extractionThe ether extract
10. washwas washed with saturated NaCl solution
11. dry with materialdried over Na2SO4
12. filtrationfiltered
13. concentrationconcentrated in vacuo
14. customThe product (26.0 g) was recrystallized from n-butyl chloride (100mL) and petroleum ether (100 mL)
15. customWeight of light tan solid recovered

ORD record

ord-d957b311ff9247ef83d568fe1d46a534

Source dataset

uspto-grants-1995_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05453424