Reacción #487539

Ecuación de reacción

hydrochloric acid

N-methoxy-N-methyldecanamide

magnesium

1-bromononane

→

10-nonadecanone

Rendimiento 95.0%

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas heated
2. 2
   TemperaturaAfter heating
3. 3
   Temperaturato reflux for 1.5 hours
4. 4
   Otroobtained by the method
5. 5
   Extracciónfollowed by extraction with diethyl ether two times
6. 6
   workup.ADDITIONAnhydrous magnesium sulfate was added to the organic layer
7. 7
   Otroto dry it
8. 8
   Filtraciónthe resultant was filtrated
9. 9
   Concentraciónwas then concentrated
10. 10
    OtroThe obtained residue was purified

Procedimiento

Polished shaved magnesium (3.2 g, 134 mmol) was heated, and thereafter, an anhydrous THF solution (68 ml) of 1-bromononane (12.9 ml, 67.5 mmol) was slowly added dropwise thereto. After heating to reflux for 1.5 hours, the reaction solution was cooled to a room temperature, and it was then added dropwise to a THF (80 mL) solution of the N-methoxy-N-methyldecanamide (4.8 g, 22.5 mmol) obtained by the method described in Production Example D-1-1. After the obtained mixture had been stirred for 30 minutes, 1 N hydrochloric acid was added to the reaction solution, followed by extraction with diethyl ether two times. Anhydrous magnesium sulfate was added to the organic layer to dry it, and the resultant was filtrated and was then concentrated. The obtained residue was purified using column chromatography (hexane:dichloromethane=8:1), so as to obtain 10-nonadecanone (6.0 g, 95%) as a ketone body in the form of a white amorphous solid.

Fuente