HCID 178477796, compound → HCID 178468161, compound

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence