反应详情

温度

80 °C

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.

1. waitthe heating at 80° C. continued for 2 hours
2. temperatureThe reaction mixture is cooled
3. additionadded to 300 ml
4. extractionThe quenched mixture is extracted with two 75 ml
5. washThe extract is washed once with 50 ml
6. dry with materialof saturated sodium chloride, dried over magnesium sulfate
7. customevaporated
8. customto yield an oil
9. temperatureThe reaction mixture is refluxed for 17 hours
10. temperaturecooled in ice
11. additiondecomposed by the addition of 3 ml
12. stirringAfter stirring for 30 minutes at 25° C.
13. customthe quenched reaction mixture
14. filtrationis filtered
15. customthe filtrate evaporated to a solid
16. customRecrystallization from dichloromethane and pentane
17. customgives 296 mg