Réaction #90544

Équation de réaction

PTSA

11

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

3-(trifluoromethyl)benzaldehyde

→

crude compound 152

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

Solvants

ethyl acetate

toluene

Conditions de réaction

Traitement

1. 1
   Lavagewashed with water (3×25 mL)
2. 2
   SéchageThe organic layer was dried over sodium sulphate
3. 3
   Concentrationconcentrated

Mode opératoire

To a solution of 11 (200 mg, 0.829 mmol) in toluene was added 3-(trifluoromethyl)benzaldehyde 99 (158.86 mg, 0.9128 mmol). PTSA (285.5 mg, 172.20 mmol) was added to the reaction mass, then stirred at 120° C. for 6 h, 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 152 which was purified through flash chromatography by using 100-200 mesh silica gel. The compound (E)-5-bromo-6-methoxy-2-(3-(trifluoromethyl)benzylidene)-2,3-dihydro-1H-inden-1-one 152 was eluted at 30% ethyl acetate in hexane to afford yellow coloured solid.

Source