Réaction #9738

Équation de réaction

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

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

intermediate 35

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

sodium bromate

sodium bisulfite

→

title compound

{2-methyl-5-[4-(trifluoromethyl)phenyl]thien-3-yl}methanol

Solvants

cyclohexane

water

water

Conditions de réaction

Traitement

1. 1
   Autrequenched with 1M sodium thiosulfate solution
2. 2
   Extractionextracted with ethyl acetate
3. 3
   Lavagewashed with water, sodium thiosulfate
4. 4
   Séchagedried with brine and over MgSO4
5. 5
   Concentrationconcentrated

Mode opératoire

Ethyl 3-methyl-5-[4-(trifluoromethyl)phenyl]thiophene-2-carboxylate (intermediate 35, 0.100 g) and sodium bromate (0.144 g) were suspended in a mixture of cyclohexane and water (1:1 v/v, 4 ml). To this was added a solution sodium bisulfite (0.99 g) in water (1 ml). The mixture was stirred for 2 hours, quenched with 1M sodium thiosulfate solution, then extracted with ethyl acetate. The organic layer was taken and washed with water, sodium thiosulfate and dried with brine and over MgSO4 and concentrated to give the title compound as a white crystalline solid.

Source