Reaction #9734

Reaction equation

ethyl thioglycolate

Sodium hydride

N-{3-chloro-1-methyl-3-[4-(trifluoromethyl)phenyl]prop-2-enylidene}-N-methylmethanaminium hexafluorophosphate

intermediate 34

N-{3-chloro-1-methyl-3-[4-(trifluoromethyl)phenyl]prop-2-enylidene}-N-methylmethanaminium hexafluorophosphate

→

title compound

ethyl 3-methyl-5-[4-(trifluoromethyl)phenyl]thiophene-2-carboxylate

Solvents

ethanol

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   ConcentrationThe cooled mixture was concentrated in vacuo
3. 3
   Otherthe residue partitioned between water and diethyl ether
4. 4
   OtherThe organic layer was collected
5. 5
   Dryingdried over magnesium sulphate
6. 6
   Concentrationconcentrated

Procedure

Sodium hydride (60% dispersion in mineral oil, 0.528 g) was added to dry ethanol (20 ml), N-{3-chloro-1-methyl-3-[4-(trifluoromethyl)phenyl]prop-2-enylidene}-N-methylmethanaminium hexafluorophosphate (intermediate 34, 2.8 g) was added followed by ethyl thioglycolate (0.79 g) and the mixture heated at 110° C. for 2 hours under nitrogen. The cooled mixture was concentrated in vacuo and the residue partitioned between water and diethyl ether. The organic layer was collected, dried over magnesium sulphate and concentrated to give the title compound as a brown solid.

Source