Reacción #9736

Ecuación de reacción

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

Disolventes

water

t-butanol

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONTo this was added drop-wise
2. 2
   workup.ADDITIONAfter the addition
3. 3
   ConcentraciónThe solution was then concentrated
4. 4
   Otropartitioned between water and ethyl acetate
5. 5
   LavadoThe aqueous layer was washed with a second ethyl acetate portion
6. 6
   Lavadowashed with brine
7. 7
   Secadodried (MgSO4)
8. 8
   OtroThe solution was then absorbed onto silica
9. 9
   LavadoThe product was eluted with neat ethyl acetate

Procedimiento

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.

Fuente