Reaktion #54356

Reaktionsgleichung

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

Ausbeute 42.0%

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

Ausbeute 42.0%

Lösungsmittel

toluene

ether

pyridine

ether

water

water

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITthe heating at 80° C. continued for 2 hours
2. 2
   TemperaturThe reaction mixture is cooled
3. 3
   workup.ADDITIONadded to 300 ml
4. 4
   ExtraktionThe quenched mixture is extracted with two 75 ml
5. 5
   WaschenThe extract is washed once with 50 ml
6. 6
   Trocknenof saturated sodium chloride, dried over magnesium sulfate
7. 7
   Sonstigeevaporated
8. 8
   Sonstigeto yield an oil
9. 9
   TemperaturThe reaction mixture is refluxed for 17 hours
10. 10
    Temperaturcooled 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
    Sonstigethe quenched reaction mixture
14. 14
    Filtrationis filtered
15. 15
    Sonstigethe filtrate evaporated to a solid
16. 16
    SonstigeRecrystallization from dichloromethane and pentane
17. 17
    Sonstigegives 296 mg

Vorschrift

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.

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