Reacción #5754

Ecuación de reacción

6,10-dimethyl-11-(2-tetrahydropyranyl) oxy-5,9-undecadien-2-one

tetrahydrofuran

ammonium chloride

→

3,7,11-trimethyl-12-(2-tetrahydropyranyl)oxy-6,10-dodecadien-1-in-3-ol

Rendimiento 75.0%

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONTo the solution was added lithium acetylide ethylenediamine complex (180 mg, 1.95 mmol)
2. 2
   Extracciónthe reaction mixture was extracted with ether
3. 3
   SecadoThe extract was dried over Na2SO4
4. 4
   Otroevaporated in vacuo
5. 5
   Otroto remove the solvent
6. 6
   Otroto give a crude product, which
7. 7
   Otrowas purified with silica gel column chromatography

Procedimiento

A solution of 6,10-dimethyl-11-(2-tetrahydropyranyl) oxy-5,9-undecadien-2-one (90 mg, 0.31 mmol) in tetrahydrofuran (5 ml) was stirred on an ice bath under argon atmosphere. To the solution was added lithium acetylide ethylenediamine complex (180 mg, 1.95 mmol), and the mixture was warmed to room temperature and stirred for 3 hours. After addition of saturated aqueous ammonium chloride (2 ml), the reaction mixture was extracted with ether. The extract was dried over Na2SO4 and evaporated in vacuo to remove the solvent to give a crude product, which was purified with silica gel column chromatography to obtain 3,7,11-trimethyl-12-(2-tetrahydropyranyl)oxy-6,10-dodecadien-1-in-3-ol (75 mg, 75%).

Fuente