Reaktion #90564

Reaktionsgleichung

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

n-BuLi

hexafluoroacetone

Hexafluoroacetone

→

compound

Ausbeute 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

Ausbeute 15.5%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirred for another 2 h
2. 2
   SonstigeAfter completion of the reaction, it
3. 3
   Sonstigewas quenched with saturated ammonium chloride solution
4. 4
   SonstigeThe organic layer was separated
5. 5
   Extraktionaqueous phase was extracted again with diethyl ether
6. 6
   Trocknenthe combined organic layer was dried over sodium sulphate
7. 7
   Einengenconcentrated
8. 8
   Sonstigeto get the crude 270, which
9. 9
   Sonstigewas purified through 100-200 mesh silica gel
10. 10
    Waschenby eluting with 15% ethyl acetate in hexane

Vorschrift

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.

Quelle