Reaction #6943

Reaction equation

MeI

3-(4-Methyl-phenyl)-3-oxo-propionitrile

K2CO3

1-chloro-propan-2-one

CS2

→

desired product

5-Acetyl-2-methylsulfanyl-4-(4-methyl-phenyl)-thiophene-3-carbonitrile

Solvents

DMF

DMF

DMF

Conditions

Workup

1. 1
   workup.STIRRINGthe resulting mixture stirred at room temperature for an additional 10 minutes
2. 2
   workup.WAITAfter 1 hour
3. 3
   workup.WAITAfter 30 minutes
4. 4
   workup.ADDITIONthe mixture was poured onto water
5. 5
   workup.STIRRINGthe resulting mixture was stirred vigorously for 12–16 hours
6. 6
   Otherto afford

Procedure

3-(4-Methyl-phenyl)-3-oxo-propionitrile (5 mmol) was added to a suspension of K2CO3 (3 equivalents, 15 mmol) in DMF (4.5 mL) and allowed to stir at room temperature. After 10 minutes, CS2 (1.25 equivalents, 7.5 mmol) was added in one portion and the resulting mixture stirred at room temperature for an additional 10 minutes. A solution of 1-chloro-propan-2-one (1.0 equivalent, 5 mmol) in DMF (5 mL) was added. After 1 hour, a solution of MeI (1.1 equivalents, 5.5 mmol) in DMF (2 mL) was added in a dropwise fashion. After 30 minutes, the mixture was poured onto water and the resulting mixture was stirred vigorously for 12–16 hours to afford a suspension of the desired product. The crude product was isolated by filtration.

Source