Reacción #6084

Ecuación de reacción

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

Disolventes

diethyl ether

ether

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroA 250 ml 3-necked flask is fitted with a stirrer, a dropping funnel, a nitrogen inlet
2. 2
   Otrodoes not exceed -60° C
3. 3
   Otroto rise to room temperature
4. 4
   FiltraciónThe mixture is then filtered
5. 5
   Lavadothe residue washed with ether
6. 6
   LavadoThe ether layer is then washed with saturated sodium chloride solution
7. 7
   Secadodried (MgSO4)
8. 8
   Concentraciónconcentrated in vacuo
9. 9
   OtroThe residue is purified by chromatography
10. 10
    Otrofollowed by recrystallization

Procedimiento

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.

Fuente