Реакция #487539

Уравнение реакции

hydrochloric acid

N-methoxy-N-methyldecanamide

magnesium

1-bromononane

→

10-nonadecanone

Выход 95.0%

Растворители

THF

THF

Условия реакции

Обработка

1. 1
   Температураwas heated
2. 2
   ТемператураAfter heating
3. 3
   Температураto reflux for 1.5 hours
4. 4
   Другоеobtained by the method
5. 5
   Экстракцияfollowed by extraction with diethyl ether two times
6. 6
   workup.ADDITIONAnhydrous magnesium sulfate was added to the organic layer
7. 7
   Другоеto dry it
8. 8
   Фильтрацияthe resultant was filtrated
9. 9
   Концентрированиеwas then concentrated
10. 10
    ДругоеThe obtained residue was purified

Методика

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.

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