Réaction #487539

Équation de réaction

hydrochloric acid

N-methoxy-N-methyldecanamide

magnesium

1-bromononane

→

10-nonadecanone

Rendement 95.0%

Solvants

THF

THF

Conditions de réaction

Traitement

1. 1
   Températurewas heated
2. 2
   TempératureAfter heating
3. 3
   Températureto reflux for 1.5 hours
4. 4
   Autreobtained by the method
5. 5
   Extractionfollowed by extraction with diethyl ether two times
6. 6
   workup.ADDITIONAnhydrous magnesium sulfate was added to the organic layer
7. 7
   Autreto dry it
8. 8
   Filtrationthe resultant was filtrated
9. 9
   Concentrationwas then concentrated
10. 10
    AutreThe obtained residue was purified

Mode opératoire

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.

Source