Reacción #90563

Ecuación de reacción

13

6-methoxy-5-morpholino-2,3-dihydro-1H-inden-1-one

6-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)picolinaldehyde

NaOH

→

(E)-2-((6-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)pyridin-2-yl)methylene)-6-methoxy-5-morpholino-2,3-dihydro-1H-inden-1-one

Disolventes

MeOH H2O

chloroform

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowashed with water (3×25 ml)
2. 2
   SecadoThe organic layer was dried over sodium sulphate
3. 3
   Concentraciónconcentrated
4. 4
   Otroto get the crude, which
5. 5
   Otrowas purified through flash chromatography
6. 6
   LavadoThe compound 265 was eluted at 30% ethyl acetate in hexane

Procedimiento

To a solution of 13 (0.1 g, 0.40 mmol)) in MeOH/H2O (1:1) was added 6-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)picolinaldehyde 262 (0.132 g, 0.485 mmol), NaOH (0.032 g, 0.80 mmol), and the reaction stirred at RT for 6 h. The reaction mass was diluted with chloroform and washed with water (3×25 ml). The organic layer was dried over sodium sulphate and concentrated to get the crude, which was purified through flash chromatography by using 100-200 mesh silica gel. The compound 265 was eluted at 30% ethyl acetate in hexane to afford yellow coloured solid (E)-2-((6-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)pyridin-2-yl)methylene)-6-methoxy-5-morpholino-2,3-dihydro-1H-inden-1-one 265.

Fuente