반응 #9736

반응 방정식

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

용매

water

t-butanol

반응 조건

후처리

1. 1
   workup.ADDITIONTo this was added drop-wise
2. 2
   workup.ADDITIONAfter the addition
3. 3
   농축The solution was then concentrated
4. 4
   기타partitioned between water and ethyl acetate
5. 5
   세척The aqueous layer was washed with a second ethyl acetate portion
6. 6
   세척washed with brine
7. 7
   건조dried (MgSO4)
8. 8
   기타The solution was then absorbed onto silica
9. 9
   세척The product was eluted with neat ethyl acetate

실험 절차

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.

출처