Реакция #9763

Уравнение реакции

NaHCO3

4-methoxy-3-methyl-phenylacetic acid

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

intermediate 102

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

methanesulfonic acid

P2O5

→

title compound

2-(4-methoxy-3-methylphenyl)-1-{3-methyl-5-[4-(trifluoromethyl)phenyl]thien-2-yl}ethanone

Растворители

water

Условия реакции

Обработка

1. 1
   Другоеformed
2. 2
   ТемператураThe mixture was cooled to room temperature
3. 3
   ТемператураThe mixture was then heated to 60° C. for 90 minutes
4. 4
   ТемператураThe reaction mixture was cooled to room temperature
5. 5
   Экстракцияthe products extracted into ethyl acetate
6. 6
   СушкаThe combined organic extracts were dried (MgSO4)
7. 7
   Фильтрацияfiltered
8. 8
   Другоеevaporated
9. 9
   Другоеto yield a brown oil
10. 10
    ДругоеPurification by flash column chromatography
11. 11
    Промывкаeluting with 5% EtOAc/cyclohexane

Методика

To methanesulfonic acid (8 ml) in a flask under N2 was added P2O5 (0.56 g), the resulting suspension was heated to 60° C. until a clear solution formed. The mixture was cooled to room temperature prior to addition of 4-methoxy-3-methyl-phenylacetic acid (0.3549) and 4-methyl-2-[4-(trifluoromethyl)phenyl]thiophene (intermediate 102, 0.4 g). The mixture was then heated to 60° C. for 90 minutes. The reaction mixture was cooled to room temperature and then poured into iced water. The suspension was made basic by cautious addition of NaHCO3 and the products extracted into ethyl acetate. The combined organic extracts were dried (MgSO4), filtered and evaporated to yield a brown oil. Purification by flash column chromatography eluting with 5% EtOAc/cyclohexane yielded the title compound as a brown gum.

Источник