Cyclohexanone → HCID 14021212, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of sodium hydide (4.07 g, 60%, 101 mmol) in THF (100) is cooled to 0° C. Two addition funnels are charged with ethyl isocyanoacetate (10.0 g, 88.4 mmol) in THF (10 mL) and cyclohexanone (9.67 g, 88.4 mmol) in THF (10 mL). The solutions are added dropwise to the reaction mixture over a 30 minute period. The resulting mixture is then allowed to warm to room temperature and stirred overnight. The reaction mixture is quenched by the addition of saturated ammonium chloride solution. The layers are separated, and the aqueous layer is washed with ethyl acetate (3×100 mL). The combined organic extracts are washed with brine (200 mL), dried (MgSO4) and then concentrated to an oil under reduced pressure. Ethyl acetate (40 mL) followed by hexane is added to the mixture until the mixture became turbid. The resulting solution is cooled to 0° C. and the desired product crystallized out of solution.

Provenance & Evidence