Reacción #40916

Ecuación de reacción

water

potassium tert-butylate

(Methoxymethyl)triphenylphosphonium chloride

4-[dimethylaminomethyl]-cyclohexanone

water

→

4-[dimethylaminomethyl]-cyclohexane-carbaldehyde

Disolventes

THF

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   workup.ADDITIONwas then added dropwise to the above solution
3. 3
   workup.STIRRINGstirred overnight at RT
4. 4
   workup.STIRRINGAfter stirring for one hour at RT the mixture
5. 5
   Extracciónwas extracted with ether (10×50 ml)
6. 6
   workup.STIRRINGshaken with ethyl acetate (3×50 ml)
7. 7
   Secadodried over Na2SO4
8. 8
   Concentraciónconcentrated by evaporation in vacuo
9. 9
   OtroThe crude product was purified by flash chromatography with ethyl acetate/cyclohexane (1:1)
10. 10
    OtroAs a rule two diastereomers were obtained in different ratios

Procedimiento

(Methoxymethyl)triphenylphosphonium chloride (25.7 g, 75 mmole) was suspended in absolute THF (100 ml) under argon, potassium tert-butylate (8.42 g, 75 mmole) dissolved in absolute THF (70 ml) was added dropwise, and then stirred for 15 minutes at 0° C. The corresponding 4-[dimethylaminomethyl]-cyclohexanone 8 (50 mmole), dissolved in absolute THF (75 ml), was then added dropwise to the above solution and stirred overnight at RT. The mixture was hydrolysed by adding dropwise water (38 ml) and 6N HCL 112 ml) while cooling with iced water. After stirring for one hour at RT the mixture was extracted with ether (10×50 ml), the aqueous phase was adjusted to pH 11 with 5N NaOH, shaken with ethyl acetate (3×50 ml), dried over Na2SO4, and concentrated by evaporation in vacuo. The crude product was purified by flash chromatography with ethyl acetate/cyclohexane (1:1). As a rule two diastereomers were obtained in different ratios.

Fuente