Реакция #90564

Уравнение реакции

2-(2-chloro-5-(trifluoromethyl)benzyl)-6-methoxy-5-morpholino-2,3-dihydro-1H-inden-1-one

n-BuLi

hexafluoroacetone

Hexafluoroacetone

→

compound

Выход 15.5%

2-(2-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-5-(trifluoromethyl)benzyl)-6-methoxy-5-morpholino-2,3-dihydro-1H-inden-1-one

Выход 15.5%

Растворители

THF

Условия реакции

Обработка

1. 1
   workup.STIRRINGstirred for another 2 h
2. 2
   ДругоеAfter completion of the reaction, it
3. 3
   Другоеwas quenched with saturated ammonium chloride solution
4. 4
   ДругоеThe organic layer was separated
5. 5
   Экстракцияaqueous phase was extracted again with diethyl ether
6. 6
   Сушкаthe combined organic layer was dried over sodium sulphate
7. 7
   Концентрированиеconcentrated
8. 8
   Другоеto get the crude 270, which
9. 9
   Другоеwas purified through 100-200 mesh silica gel
10. 10
    Промывкаby eluting with 15% ethyl acetate in hexane

Методика

To a stirred solution of 2-(2-chloro-5-(trifluoromethyl)benzyl)-6-methoxy-5-morpholino-2,3-dihydro-1H-inden-1-one 269 (0.1 g, 0.226 mmol) in dry THF, cooled to 0° C., n-BuLi (0.021 g, 0.339 mmol) was added drop wise and the solution stirred for 10 min. Then hexafluoroacetone 244 (0.10 g, 0.453 mmol) was added to the reaction and stirred for another 2 h. After completion of the reaction, it was quenched with saturated ammonium chloride solution. The organic layer was separated and aqueous phase was extracted again with diethyl ether, the combined organic layer was dried over sodium sulphate and concentrated to get the crude 270, which was purified through 100-200 mesh silica gel by eluting with 15% ethyl acetate in hexane to give 20 mg of compound 2-(2-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-5-(trifluoromethyl)benzyl)-6-methoxy-5-morpholino-2,3-dihydro-1H-inden-1-one 270.

Источник