Reacción #76823

Ecuación de reacción

hydrochloric acid

aluminum isopropoxide

3-nitrobenzaldehyde

(2E,6E)-3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol

→

title compound

Rendimiento 96.0%

(2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrien-1-al

Rendimiento 96.0%

Disolventes

hexane

cyclohexane

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted twice with ethyl acetate
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=9:1)

Procedimiento

(2E,6E)-3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol (445 mg, 2.0 mmol) was dissolved in cyclohexane (1 mL), added with aluminum isopropoxide (40 mg, 0.1 eq, 0.2 mmol) and 3-nitrobenzaldehyde (393 mg, 1.3 eq, 2.6 mmol) and stirred at room temperature for 2 hours. The reaction mixture was added with hexane, then made acidic with addition of 1 N hydrochloric acid and extracted twice with ethyl acetate. 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=9:1) to obtain 427 mg (yield: 96%, E:Z=99:1) of the title compound as yellow oil.

Fuente