Reacción #90519

Ecuación de reacción

13

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

3-bromo-2, 6-difluorobenzaldehyde

PTSA

→

crude compound 41

(E)-2-(3-bromo-2,6-difluorobenzylidene)-6-methoxy-5-morpholino-2,3-dihydro-1H-inden-1-one

Disolventes

toluene

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added
2. 2
   Lavadowashed with water (3×25 mL)
3. 3
   SecadoThe organic layer was dried over sodium sulphate
4. 4
   Concentraciónconcentrated

Procedimiento

To a solution of 13 (150 mg, 0.607 mmol) in toluene 15 mL was added 3-bromo-2, 6-difluorobenzaldehyde 40 (81.4 mg, 0.607 mmol) and subsequently PTSA (230.9 mg, 1.214 mmol) was added, and stirred at 120° C. for 6 h. The reaction mass was diluted with ethyl acetate and washed with water (3×25 mL). The organic layer was dried over sodium sulphate and concentrated to get the crude compound 41. The crude 41 was purified through flash chromatography by using 100-200 mesh silica gel. The compound (E)-2-(3-bromo-2,6-difluorobenzylidene)-6-methoxy-5-morpholino-2,3-dihydro-1H-inden-1-one 41 was eluted at 32% ethyl acetate in hexane to afford yellow coloured solid.

Fuente