Réaction #5755

Équation de réaction

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

tetrahydrofuran

ammonium chloride

→

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

Rendement 83.0%

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONTo the solution was added lithium acetylide ethylenediamine complex (30 mg, 0.33 mmol)
2. 2
   Extractionthe reaction mixture was extracted with ether
3. 3
   SéchageThe extract was dried over Na2SO4
4. 4
   Autreevaporated in vacuo
5. 5
   Autreto remove the solvent
6. 6
   Autreto give a crude product, which
7. 7
   Autrewas purified with silica gel column chromatography

Mode opératoire

A solution of 6,10-dimethyl-11-(methoxymethyl)oxy-5,9-undecadien-2-one (67 mg, 0.26 mmol) in tetrahydrofuran (2 ml) was stirred on an ice bath under argon atmosphere. To the solution was added lithium acetylide ethylenediamine complex (30 mg, 0.33 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-(methoxymethyl)oxy-6,10-dodecadien-1-in- 3-ol (61 mg, 83%).

Source