Reacción #158335

Ecuación de reacción

ammonium chloride

3,4-Dichlorophenylmagnesium bromide

6-[3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl]hex-5-ynal

3,4-Dichlorophenylmagnesium bromide

→

title compound

1-(3,4-dichlorophenyl)-6-[3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl]hex-5-yn-1-ol

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooling
2. 2
   workup.STIRRINGthe mixture was stirred for 1 hr under ice-
3. 3
   Temperaturacooling
4. 4
   Extracciónthe mixture was extracted with ethyl acetate
5. 5
   LavadoThe extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
6. 6
   Secadodried over anhydrous sodium sulfate
7. 7
   Otrothe solvent was evaporated under reduced pressure
8. 8
   OtroThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Procedimiento

3,4-Dichlorophenylmagnesium bromide (0.5 M THF solution, 13 mL) was added dropwise to a mixture of 6-[3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl]hex-5-ynal (900 mg) in THF (32 mL) at −78° C., and the mixture was stirred for 1 hr under ice-cooling and at room temperature for 14 hr. 3,4-Dichlorophenylmagnesium bromide (0.5M THF solution, 13 mL) was added to the reaction mixture under ice-cooling, and the mixture was stirred for 1 hr under ice-cooling. Saturated aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (349 mg).

Fuente