反応 #5758

反応方程式

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

vinylmagnesium bromide

ammonium chloride

→

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

収率 80.0%

溶媒

tetrahydrofuran

tetrahydrofuran

反応条件

後処理

1. 1
   抽出the reaction mixture was extracted with ether
2. 2
   乾燥The extract was dried over Na2SO4
3. 3
   その他evaporated in vacuo
4. 4
   その他to remove the solvent
5. 5
   その他to give a crude product, which
6. 6
   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 (60 mg, 0.24 mmol) in tetrahydrofuran (2 ml) was stirred on an ice bath under argon atmosphere. To the solution was added vinylmagnesium bromide in tetrahydrofuran (1.0 ml, 1.0 mmol, 1.0 M), and the mixture was warmed to room temperature and stirred for 4 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-1,6,10-dodecatrien-3-ol (54 mg, 80%).

出典