Reacción #76827

Ecuación de reacción

hydrochloric acid

aluminum isopropoxide

2-nitrobenzaldehyde

(2Z)-3,7-Dimethyl-2,6-octadien-1-ol

→

title compound

Rendimiento 83.0%

(2Z)-3,7-dimethyl-2,6-octadien-1-al

Rendimiento 83.0%

Disolventes

ethyl acetate

benzene

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe organic layer was separated
2. 2
   LavadoSubsequently, the organic layer was washed with saturated brine
3. 3
   Secadodried over magnesium sulfate
4. 4
   OtroThe solvent was evaporated in vacuo
5. 5
   Otrothe residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1)

Procedimiento

(2Z)-3,7-Dimethyl-2,6-octadien-1-ol (310 mg, 2.0 mmol) was dissolved in benzene (1 mL), added with aluminum isopropoxide (40 mg, 0.1 eq, 0.20 mmol) and 2-nitrobenzaldehyde (390 mg, 1.3 eq, 2.6 mmol) and stirred at room temperature for 1 hour and 30 minutes. The reaction mixture was added with ethyl acetate and made acidic with addition of 2 N hydrochloric acid, and then the organic layer was separated. Subsequently, the organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated in vacuo, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1) to obtain 250 mg (yield: 83%, E:Z=9:10) of the title compound as yellow oil.

Fuente