Reaktion #5757

Reaktionsgleichung

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

Ausbeute 70.0%

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe reaction mixture was extracted with ether
2. 2
   TrocknenThe extract was dried over Na2SO4
3. 3
   Sonstigeevaporated in vacuo
4. 4
   Sonstigeto remove the solvent
5. 5
   Sonstigeto give a crude product, which
6. 6
   Sonstigewas purified with silica gel column chromatography

Vorschrift

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, 1.0 M), 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%). IR(film)cm-1 ; 3460, 2950, 2880, 1200, 1118, 1075, 1022, 905, 865, 810.

Quelle