反应 #54339

反应方程式

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

ammonium chloride

magnesium

N-benzyl-3-piperidone

→

title compound

收率 67.0%

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

收率 67.0%

溶剂

ether

tetrahydrofuran

tetrahydrofuran

反应条件

后处理

1. 1
   温度The resulting mixture is refluxed for 20 minutes
2. 2
   温度is maintained below 0° C
3. 3
   workup.ADDITIONcompletion of addition
4. 4
   workup.ADDITIONis then added to 500 ml
5. 5
   萃取The ether extract
6. 6
   洗涤is washed with two 250 ml
7. 7
   干燥portions of sodium chloride, dried over magnesium sulfate
8. 8
   其他evaporated to an oil
9. 9
   其他The oil is purified via column chromatography on 700 g
10. 10
    洗涤of silica gel eluted with 50% ether-cyclohexane
11. 11
    其他to yield 17.1 g

实验过程

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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