反应 #6084

反应方程式

ethyl 6-[2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)ethynyl]-nicotinoate

lithium aluminum hydride

hydride

ethyl acetate

ammonium chloride

→

title compound

2-[2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)ethynyl]-5-hydroxymethylpyridine

溶剂

diethyl ether

ether

反应条件

后处理

1. 1
   其他A 250 ml 3-necked flask is fitted with a stirrer, a dropping funnel, a nitrogen inlet
2. 2
   其他does not exceed -60° C
3. 3
   其他to rise to room temperature
4. 4
   过滤The mixture is then filtered
5. 5
   洗涤the residue washed with ether
6. 6
   洗涤The ether layer is then washed with saturated sodium chloride solution
7. 7
   干燥dried (MgSO4)
8. 8
   浓缩concentrated in vacuo
9. 9
   其他The residue is purified by chromatography
10. 10
    其他followed by recrystallization

实验过程

A 250 ml 3-necked flask is fitted with a stirrer, a dropping funnel, a nitrogen inlet and a thermometer. In the flask is placed a solution of 379.5 mg (10 mmol) of lithium aluminum hydride in 30 ml of dry diethyl ether. The solution is cooled to -65° C. under nitrogen and a solution of 3.6148 g (10 mmol) of ethyl 6-[2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphth-2-yl)ethynyl]-nicotinoate in 15 ml of dry ether is added dropwise at a rate such that the temperature does not exceed -60° C. The mixture is stirred at -30° C. for 1 hour and the excess hydride is then destroyed by the addition of 300 mg (3.4 mmol) of ethyl acetate. The reaction mixture is then hydrolyzed by adding 3 ml of saturated ammonium chloride solution and allowing the temperature to rise to room temperature. The mixture is then filtered and the residue washed with ether. The ether layer is then washed with saturated sodium chloride solution, dried (MgSO4) and then concentrated in vacuo. The residue is purified by chromatography followed by recrystallization to give the title compound.

来源