2-Ethyl-1-butanol → HCID 66746599, compound

Temperature

0 °C

To a solution of 2-ethylbutan-1-ol (1.02 g, 10.0 mmol) in dry THF (60 mL) was carefully added NaH (60% in mineral oil, 480 mg, 12.0 mmol) in small portions at 0° C. under nitrogen. The reaction mixture was stirred at 0° C. under nitrogen for 2 hrs. To this solution was added 2-amino-6-fluorobenzonitrile (1.36 g, 10.0 mmol), and the reaction solution was stirred at 0° C.—RT for 2 hrs, and then at 65° C. overnight under nitrogen. The reaction was cooled down to room temperature then quenched with brine, and extracted with EtOAc (3×). The combined organic layers were washed with brine, dried over Na2SO4. Filtered and evaporated under reduced pressure. The residue was purified by chromatography on silica gel (eluent: 20% EtOAc in hexanes) to give the title compound as colorless oil (1.29 g, 59%). 1H NMR (400 MHz, CDCl3) δ 0.93 (t, J=8 Hz, 6H), 1.55-1.43 (m, 4H), 1.73-1.65 (m, 1H), 3.90 (d, J=4 Hz, 2H), 4.10 (brs, 2H), 6.25 (d, J=8 Hz, 1H), 6.34 (d, J=8 Hz, 1H), 7.20 (t, J=8 Hz, 1H).

1. customat 0° C.
2. stirringthe reaction solution was stirred at 0° C.—RT for 2 hrs
3. customat 65° C.
4. customovernight
5. temperatureThe reaction was cooled down to room temperature
6. customthen quenched with brine
7. extractionextracted with EtOAc (3×)
8. washThe combined organic layers were washed with brine
9. dry with materialdried over Na2SO4
10. filtrationFiltered
11. customevaporated under reduced pressure
12. customThe residue was purified by chromatography on silica gel (eluent: 20% EtOAc in hexanes)

ORD record

ord-e238b445c9504492a43e6fc2cc73a435

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09000054B2