Reaction #6955

Reaction equation

Iodomethane

chloroacetone

3-cyclohexyl-3-oxo-propionitrile

K2CO3

DMF CS2

→

5-Acetyl-4-cyclohexyl-2-methylsulfanyl-thiophene-3-carbonitrile

Conditions

Workup

1. 1
   OtherTo the resulting reaction mixture
2. 2
   workup.STIRRINGthe reaction mixture stirred at ambient temperature for 3 hours
3. 3
   workup.STIRRINGthe resulting mixture was stirred at ambient temperature overnight
4. 4
   OtherThe reaction mixture was partitioned between ethyl acetate and brine
5. 5
   Dryingthe organic phase dried with MgSO4
6. 6
   Otherthe solvent was removed under reduced pressure
7. 7
   OtherThe crude product was purified by silica gel chromatography

Procedure

To a solution of 3-cyclohexyl-3-oxo-propionitrile in DMF:CS2 (1:1) was added K2CO3 at 0° C. and the reaction mixture stirred at ambient temperature for 2 hours. To the resulting reaction mixture was added chloroacetone (1 equivalent) and the reaction mixture stirred at ambient temperature for 3 hours. Iodomethane was then added and the resulting mixture was stirred at ambient temperature overnight. The reaction mixture was partitioned between ethyl acetate and brine, the organic phase dried with MgSO4 and the solvent was removed under reduced pressure. The crude product was purified by silica gel chromatography.

Source