Reacción #1794960

Ecuación de reacción

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

vinylmagnesium bromide

ammonium chloride

→

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

Rendimiento 70.0%

Disolventes

tetrahydrofuran

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónthe reaction mixture was extracted with ether
2. 2
   SecadoThe extract was dried over Na2SO4
3. 3
   Otroevaporated in vacuo
4. 4
   Otroto remove the solvent
5. 5
   Otroto give a crude product, which
6. 6
   Otrowas purified with silica gel column chromatography

Procedimiento

A solution of 6,10-dimethyl-11-(2-tetrahydropyranyl) oxy-5,9-undecadien-2-one (80 mg, 0.27 mmol) in tetrahydrofuran (3 ml) was stirred on an ice bath under argon atmosphere. To the solution was added vinylmagnesium bromide in tetrahydrofuran (0.3 ml, 0.3 mmol, 1.0M), and the mixture was warmed to room temperature and stirred for 10 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-1,6,10-dodecatrien-3-ol (61 mg, 70%).

Fuente