반응 #6084

반응 방정식

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

용매

diethyl ether

ether

반응 조건

후처리

1. 1
   기타A 250 ml 3-necked flask is fitted with a stirrer, a dropping funnel, a nitrogen inlet
2. 2
   기타does not exceed -60° C
3. 3
   기타to rise to room temperature
4. 4
   여과The mixture is then filtered
5. 5
   세척the residue washed with ether
6. 6
   세척The ether layer is then washed with saturated sodium chloride solution
7. 7
   건조dried (MgSO4)
8. 8
   농축concentrated in vacuo
9. 9
   기타The residue is purified by chromatography
10. 10
    기타followed by recrystallization

실험 절차

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.

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