Réaction #9736

Équation de réaction

sodium chlorite

4-[4-(trifluoromethyl)phenyl]thiophene-2-carbaldehyde

intermediate 37

4-[4-(trifluoromethyl)phenyl]thiophene-2-carbaldehyde

2-methyl-2-butene

sodium dihydrogen phosphate

→

title compound

4-[4-(trifluoromethyl)phenyl]thiophene-2-carboxylic acid

Solvants

water

t-butanol

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONTo this was added drop-wise
2. 2
   workup.ADDITIONAfter the addition
3. 3
   ConcentrationThe solution was then concentrated
4. 4
   Autrepartitioned between water and ethyl acetate
5. 5
   LavageThe aqueous layer was washed with a second ethyl acetate portion
6. 6
   Lavagewashed with brine
7. 7
   Séchagedried (MgSO4)
8. 8
   AutreThe solution was then absorbed onto silica
9. 9
   LavageThe product was eluted with neat ethyl acetate

Mode opératoire

A solution of 4-[4-(trifluoromethyl)phenyl]thiophene-2-carbaldehyde (intermediate 37, 1.23 g), t-butanol (20 ml) and 2-methyl-2-butene (10 ml) was cooled to 0° C. To this was added drop-wise, a solution of sodium chlorite (3.8 g) and sodium dihydrogen phosphate (4.03 g) in water (15 ml). After the addition was complete, the mixture was allowed to warm to room temperature and was stirred for 4 hours. The solution was then concentrated and partitioned between water and ethyl acetate. The aqueous layer was washed with a second ethyl acetate portion and the organic liquors were combined, washed with brine, then dried (MgSO4). The solution was then absorbed onto silica and loaded onto a SPE (Si) cartridge. The product was eluted with neat ethyl acetate to afford the title compound as a white solid.

Source