Reaction #487539

Reaction equation

hydrochloric acid

N-methoxy-N-methyldecanamide

magnesium

1-bromononane

→

10-nonadecanone

Yield 95.0%

Solvents

THF

THF

Conditions

Workup

1. 1
   Temperaturewas heated
2. 2
   TemperatureAfter heating
3. 3
   Temperatureto reflux for 1.5 hours
4. 4
   Otherobtained 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
   Otherto dry it
8. 8
   Filtrationthe resultant was filtrated
9. 9
   Concentrationwas then concentrated
10. 10
    OtherThe obtained residue was purified

Procedure

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