Reaktion #5754

Reaktionsgleichung

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

Ausbeute 75.0%

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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%).

Quelle