HCID 178477796, compound → HCID 178468161, compound

Temperature

38 °C

To the product from step 1 (1.44 g, 8.42 mmol) was added dioxane (56 mL) and the solution was degassed via subsurface bubbling with argon for 30 minutes. Pd(OAc)2 (95 mg, 0.42 mmol) was added and argon was bubbled through the solution for 15 minutes. Dimethylzinc (2.0 M in toluene, 4.21 mL, 8.42 mmol) was added and the solution was evacuated and then purged with argon 5 times. The reaction was heated overnight at 38° C. The mixture was then cooled to room temperature, diluted carefully with water and ethyl acetate, filtered through a pad of CELITE and washed with ethyl acetate. The organic layer of the filtrate was then dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel to afford trans-4-acetylcyclohexanecarbonitrile. 1H NMR (500 MHz, CDCl3) δ 2.52-2.32 (m, 2H), 2.23-2.12 (m, 5H), 2.07-1.93 (m, 2H), 1.72-1.53 (m, 2H), 1.48-1.33 (m, 2H).

1. customthe solution was degassed via subsurface
2. custombubbling with argon for 30 minutes
3. customargon was bubbled through the solution for 15 minutes
4. customthe solution was evacuated
5. custompurged with argon 5 times
6. temperatureThe mixture was then cooled to room temperature
7. additiondiluted carefully with water and ethyl acetate
8. filtrationfiltered through a pad of CELITE
9. washwashed with ethyl acetate
10. dry with materialThe organic layer of the filtrate was then dried over magnesium sulfate
11. filtrationfiltered
12. concentrationconcentrated in vacuo
13. customThe residue was purified by column chromatography on silica gel

ORD record

ord-4fbd9af0de8143d9a2ccc4433bd347a1

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09290490B2