反応 #54356

反応方程式

3-[4-(1,1-dimethylheptyl)-2-hydroxyphenyl]-1,2,5,6-tetrahydropyridine

lithium aluminum hydride

cyclopropanecarboxylic acid chloride

sodium chloride

sodium hydroxide

cyclopropanecarboxylic acid chloride

→

title compound

収率 42.0%

1-N-Cyclopropylmethyl-3-[4-(1,1-dimethylheptyl)-2-hydroxyphenyl]-1,2,5,6-tetrahydropyridine

収率 42.0%

溶媒

toluene

ether

pyridine

ether

water

water

toluene

反応条件

後処理

1. 1
   workup.WAITthe heating at 80° C. continued for 2 hours
2. 2
   温度The reaction mixture is cooled
3. 3
   workup.ADDITIONadded to 300 ml
4. 4
   抽出The quenched mixture is extracted with two 75 ml
5. 5
   洗浄The extract is washed once with 50 ml
6. 6
   乾燥of saturated sodium chloride, dried over magnesium sulfate
7. 7
   その他evaporated
8. 8
   その他to yield an oil
9. 9
   温度The reaction mixture is refluxed for 17 hours
10. 10
    温度cooled in ice
11. 11
    workup.ADDITIONdecomposed by the addition of 3 ml
12. 12
    workup.STIRRINGAfter stirring for 30 minutes at 25° C.
13. 13
    その他the quenched reaction mixture
14. 14
    ろ過is filtered
15. 15
    その他the filtrate evaporated to a solid
16. 16
    その他Recrystallization from dichloromethane and pentane
17. 17
    その他gives 296 mg

実験手順

To a solution of 596 mg. (1.98 mmoles) of 3-[4-(1,1-dimethylheptyl)-2-hydroxyphenyl]-1,2,5,6-tetrahydropyridine in 2.25 ml. of toluene and 4.5 ml. of pyridine is added 180 μl (3.96 mmoles) of cyclopropanecarboxylic acid chloride in 2.25 ml. of toluene. The reaction mixture is stirred for one hour at 25° C. and for 0.5 hour at 80° C. Another 180 μl (3.96 mmoles) portion of cyclopropanecarboxylic acid chloride is added and the heating at 80° C. continued for 2 hours. The reaction mixture is cooled and added to 300 ml. of saturated sodium chloride. The quenched mixture is extracted with two 75 ml. portions of dichloromethane. The extract is washed once with 50 ml. of saturated sodium chloride, dried over magnesium sulfate and evaporated to yield an oil. A solution of this oil in 100 ml. of ether is added dropwise to a mixture of 3.0 g. (78.9 mmoles) of lithium aluminum hydride in 150 ml. of ether. The reaction mixture is refluxed for 17 hours, cooled in ice and decomposed by the addition of 3 ml. of water, 3 ml. of 15% sodium hydroxide and 9 ml. more of water. After stirring for 30 minutes at 25° C. the quenched reaction mixture is filtered and the filtrate evaporated to a solid. Recrystallization from dichloromethane and pentane gives 296 mg. (42%) of the title compound.

出典