Cyclohexanone → HCID 14021212, compound

Temperature

0 °C

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.

1. additionTwo addition funnels
2. additionThe solutions are added dropwise to the reaction mixture over a 30 minute period
3. temperatureto warm to room temperature
4. customThe reaction mixture is quenched by the addition of saturated ammonium chloride solution
5. customThe layers are separated
6. washthe aqueous layer is washed with ethyl acetate (3×100 mL)
7. washThe combined organic extracts are washed with brine (200 mL)
8. dry with materialdried (MgSO4)
9. concentrationconcentrated to an oil under reduced pressure
10. additionis added to the mixture until the mixture
11. temperatureThe resulting solution is cooled to 0° C.
12. customthe desired product crystallized out of solution

ORD record

ord-94a68c28a5ed46b79f80acb2baa0dda5

Source dataset

uspto-grants-2001_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06218389B1