Реакция #54339

Уравнение реакции

1-bromo-2-benzyloxy-4-(1,1-dimethylheptyl)benzene

ammonium chloride

magnesium

N-benzyl-3-piperidone

→

title compound

Выход 67.0%

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

Выход 67.0%

Растворители

ether

tetrahydrofuran

tetrahydrofuran

Условия реакции

Обработка

1. 1
   ТемператураThe resulting mixture is refluxed for 20 minutes
2. 2
   Температураis maintained below 0° C
3. 3
   workup.ADDITIONcompletion of addition
4. 4
   workup.ADDITIONis then added to 500 ml
5. 5
   ЭкстракцияThe ether extract
6. 6
   Промывкаis washed with two 250 ml
7. 7
   Сушкаportions of sodium chloride, dried over magnesium sulfate
8. 8
   Другоеevaporated to an oil
9. 9
   ДругоеThe oil is purified via column chromatography on 700 g
10. 10
    Промывкаof silica gel eluted with 50% ether-cyclohexane
11. 11
    Другоеto yield 17.1 g

Методика

A solution of 20.0 g. (51.4 mmols) of 1-bromo-2-benzyloxy-4-(1,1-dimethylheptyl)benzene in 75 ml. of tetrahydrofuran is slowly added to 2.5 g. (103 mmols) of 70-80 mesh magnesium metal. The resulting mixture is refluxed for 20 minutes and is then cooled to -10° C. A solution of 9.71 g. (51.4 mmols) of N-benzyl-3-piperidone in 25 ml. of tetrahydrofuran is then added at such a rate that the reaction temperature is maintained below 0° C. The reaction mixture is stirred for 30 minutes following completion of addition and is then added to 500 ml. of saturated ammonium chloride and 500 ml. of ether. The ether extract is washed with two 250 ml. portions of sodium chloride, dried over magnesium sulfate and evaporated to an oil. The oil is purified via column chromatography on 700 g. of silica gel eluted with 50% ether-cyclohexane to yield 17.1 g. (67%) of the title compound as an oil:

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