Реакция #54345

Уравнение реакции

1-benzyl-3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-piperidinol

sulfuric acid

ammonium hydroxide

acetone

→

title compound

1-Benzyl-3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-piperidone

Растворители

acetic acid

water

Условия реакции

Обработка

1. 1
   ЭкстракцияThe reaction mixture is extracted with 500 ml
2. 2
   Экстракцияof ether, the ether extract
3. 3
   Промывкаwashed once with saturated sodium chloride
4. 4
   Сушкаdried over magnesium sulfate
5. 5
   Другоеevaporated
6. 6
   ДругоеPurification
7. 7
   Промывкаof silica gel eluted with ether

Методика

To a cooled solution of 24.8 g. (50 mmols.) of 1-benzyl-3-[2-benzyloxy-4-(1,1-dimethylheptyl)phenyl]-4-piperidinol, 100 ml. of acetone, 6.0 g. (60 mmols.) of chromium trioxide, 15 ml. of water and 20 ml. of acetic acid is added dropwise 20 ml. of concentrated sulfuric acid at such a rate as to maintain the temperature at 5° C. The reaction mixture is stirred 5 hours longer (t<18° C.) and then neutralized with concentrated ammonium hydroxide. The reaction mixture is extracted with 500 ml. of ether, the ether extract washed once with saturated sodium chloride, dried over magnesium sulfate and evaporated. Purification is accomplished via rapid column chromatography on 100 g. of silica gel eluted with ether to yield the title compound.

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