反応 #5755

反応方程式

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

収率 83.0%

反応条件

後処理

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

実験手順

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%).

出典