Reacción #90564

Ecuación de reacción

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

n-BuLi

hexafluoroacetone

Hexafluoroacetone

→

compound

Rendimiento 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

Rendimiento 15.5%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGstirred for another 2 h
2. 2
   OtroAfter completion of the reaction, it
3. 3
   Otrowas quenched with saturated ammonium chloride solution
4. 4
   OtroThe organic layer was separated
5. 5
   Extracciónaqueous phase was extracted again with diethyl ether
6. 6
   Secadothe combined organic layer was dried over sodium sulphate
7. 7
   Concentraciónconcentrated
8. 8
   Otroto get the crude 270, which
9. 9
   Otrowas purified through 100-200 mesh silica gel
10. 10
    Lavadoby eluting with 15% ethyl acetate in hexane

Procedimiento

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.

Fuente