反応 #487539

反応方程式

hydrochloric acid

N-methoxy-N-methyldecanamide

magnesium

1-bromononane

→

10-nonadecanone

収率 95.0%

溶媒

THF

THF

反応条件

後処理

1. 1
   温度was heated
2. 2
   温度After heating
3. 3
   温度to reflux for 1.5 hours
4. 4
   その他obtained by the method
5. 5
   抽出followed by extraction with diethyl ether two times
6. 6
   workup.ADDITIONAnhydrous magnesium sulfate was added to the organic layer
7. 7
   その他to dry it
8. 8
   ろ過the resultant was filtrated
9. 9
   濃縮was then concentrated
10. 10
    その他The obtained residue was purified

実験手順

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.

出典