Реакция #9736

Уравнение реакции

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

Растворители

water

t-butanol

Условия реакции

Обработка

1. 1
   workup.ADDITIONTo this was added drop-wise
2. 2
   workup.ADDITIONAfter the addition
3. 3
   КонцентрированиеThe solution was then concentrated
4. 4
   Другоеpartitioned between water and ethyl acetate
5. 5
   ПромывкаThe aqueous layer was washed with a second ethyl acetate portion
6. 6
   Промывкаwashed with brine
7. 7
   Сушкаdried (MgSO4)
8. 8
   ДругоеThe solution was then absorbed onto silica
9. 9
   ПромывкаThe product was eluted with neat ethyl acetate

Методика

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.

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