Reacción #656820

Ecuación de reacción

1,2-dimethoxyethane

veratraldehyde

1,2-dimethoxyethane

sodium hydride

1,2-dimethoxyethane

dimethyl 2-oxoheptylphosphonate

→

above caption compound

1-(3,4-dimethoxyphenyl)-3-oxo-1-octene

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaafter that, cooled at -30° C
2. 2
   Otrowas restored slowly to room temperature
3. 3
   Extracciónextracted with ethyl acetate
4. 4
   LavadoThe ethyl acetate layer was washed with water
5. 5
   Secadodried with magnesium sulfate
6. 6
   OtroThe solvent was removed by distillation
7. 7
   Otroto obtain crude product
8. 8
   OtroAfter purification of the crude product by means of column chromatography (silica gel/hexane:ethyl acetate=3:1)

Procedimiento

Under cooling with ice, to 70 ml of dry 1,2-dimethoxyethane containing 0.87 g of sodium hydride (50% mineral oil) was added dropwise 30 ml of dry 1,2-dimethoxyethane containing 4.0 g of dimethyl 2-oxoheptylphosphonate. Then, the mixture was stirred at room temperature for 1 hour and, after that, cooled at -30° C. Then, 3 ml of dry 1,2-dimethoxyethane containing 3.0 g of veratraldehyde was added dropwise. After dropping, the temperature was restored slowly to room temperature. Then, the reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried with magnesium sulfate. The solvent was removed by distillation to obtain crude product. After purification of the crude product by means of column chromatography (silica gel/hexane:ethyl acetate=3:1), 1.3 g of the above caption compound was obtained.

Fuente