Réaction #1552032

Équation de réaction

Potassium t-butoxide

chloride

4-(5-propyltetrahydro-2-furanyl)cyclohexanone

→

4-(5-propyltetrahydro-2-furanyl)cyclohexanecarboaldehyde

Rendement 76.2%

Solvants

THF

THF

Conditions de réaction

Traitement

1. 1
   workup.WAITthe stirring was continued for another 1 hour
2. 2
   TempératureThe reaction mixture was warmed to room temperature
3. 3
   Autrethe mixture was separated
4. 4
   workup.ADDITIONafter the addition of water (200 ml)
5. 5
   SéchageThe organic layer was dried over anhydrous magnesium sulfate
6. 6
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
7. 7
   AutreThe residue was purified by silica gel chromatography (toluene:ethyl acetate=18:1)
8. 8
   workup.DISSOLUTIONthe resultant product was dissolved in acetone (200 ml)
9. 9
   workup.ADDITIONhydrochrolic acid (6 M) (200 ml) was added
10. 10
    workup.WAITthe stirring was continued at room temperature for another 1 hour
11. 11
    ExtractionThe mixture was extracted with toluene (100 ml)
12. 12
    workup.ADDITIONafter the addition of water (200 ml)
13. 13
    SéchageThe solution was dried over anhydrous magnesium sulfate
14. 14
    workup.DISTILLATIONthe solvent was distilled off under reduced pressure

Mode opératoire

Methoxymethyltriphenylphophnium chloride (55.23 g) and THF (300 ml) were placed in a reaction vessel, and the solution was cooled to −20° C. Potassium t-butoxide (16.0 g) was added, and the stirring was continued for another 1 hour. Then, 4-(5-propyltetrahydro-2-furanyl)cyclohexanone (15 g) in a THF (100 ml) solution was added dropwise, and the stirring was continued for another 1 hour. The reaction mixture was warmed to room temperature, and the mixture was separated after the addition of water (200 ml). The organic layer was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (toluene:ethyl acetate=18:1), and the resultant product was dissolved in acetone (200 ml) and hydrochrolic acid (6 M) (200 ml) was added, and then the stirring was continued at room temperature for another 1 hour. The mixture was extracted with toluene (100 ml) after the addition of water (200 ml). The solution was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure to give 4-(5-propyltetrahydro-2-furanyl)cyclohexanecarboaldehyde (12.2 g).

Source