Water → HCID 79137229, compound

Temperature

-70 °C

To a stirring solution of diisopropylamine (2.27 mL, 16.1 mmol) in tetrahydrofuran (60 mL) at −20° C. under nitrogen was added a solution of n-butyllithium (7.1 mL, 17.7 mmol, 2.5 M in hexane). After the addition was complete, the mixture was cooled to −70° C., isobutyryl nitrile (1.46 mL, 16.1 mmol) was added and the reaction mixture was then warmed to −10° C. After 10 minutes, 2-fluoro-benzaldehyde (1.70 mL, 16.1 mmol) was added and the resulting solution was allowed to warm to ambient temperature. After one hour at ambient temperature, water (5 mL) was added to the reaction mixture and it was concentrated at reduced pressure. The resulting crude product was diluted with ethyl acetate (125 mL), washed with water (75 mL) followed by saturated aqueous sodium chloride (50 mL) and the organic layer was concentrated at reduced pressure to give the product as a colorless oil (3.1 g, ˜100%). 1H NMR (CDCl3) δ 7.70 (m, 1H), 7.35 (m, 1H), 7.22 (m, 1H), 7.04 (m, 1H), 4.99 (br s, 1H), 2.42 (br s, 1H), 1.24 (s, 6H).

1. additionAfter the addition
2. temperaturethe reaction mixture was then warmed to −10° C
3. temperatureto warm to ambient temperature
4. waitAfter one hour at ambient temperature
5. concentrationwas concentrated at reduced pressure
6. additionThe resulting crude product was diluted with ethyl acetate (125 mL)
7. washwashed with water (75 mL)
8. concentrationthe organic layer was concentrated at reduced pressure

ORD record

ord-28c5c868c9de46e8961fe05931b45fd4

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08609849B1