反応 #452445

反応方程式

HCl

Sodium hydride

3,7-Dimethyl-1,6-octadien-3-yl 3-(β-naphthyl)-3-oxo-propionate

methyl iodide

→

desired compound

3,7-dimethyl-1,6-octadien-3-yl 3-(β-naphthyl)-3-oxo-2-methylpropionate

溶媒

tetrahydrofuran

tetrahydrofuran

反応条件

後処理

1. 1
   その他fitted with a magnetic stirrer, ice bath, addition funnel
2. 2
   workup.ADDITIONis added dropwise to the flask over 30 min
3. 3
   workup.ADDITIONDuring addition
4. 4
   workup.STIRRINGStirring
5. 5
   workup.WAITcontinues for 2 h at 0° C.
6. 6
   workup.WAITat room temperature for 18 h
7. 7
   抽出extracted with diethyl ether
8. 8
   洗浄The organic layers are washed with saturated NaHCO3 solution, water
9. 9
   乾燥dried over MgSO4
10. 10
    ろ過filtered
11. 11
    濃縮concentrated by rotary evaporation
12. 12
    その他purified by flash chromatography

実験手順

Sodium hydride (3.92 g, 0.098 mol, 60%) and tetrahydrofuran (100 mL) are placed into a 250 mL three-necked round-bottomed flask fitted with a magnetic stirrer, ice bath, addition funnel, internal thermometer and argon inlet. The contents of the flask are cooled to 0° C. 3,7-Dimethyl-1,6-octadien-3-yl 3-(β-naphthyl)-3-oxo-propionate (15.28 g, 0.044 mol) dissolved in 50 mL of tetrahydrofuran is added dropwise to the flask over 30 min. During addition, the mixture evolves gas. After stirring for 1 h, methyl iodide (10.65 g, 0.075 mol) is added to the reaction mixture. Stirring continues for 2 h at 0° C. and then at room temperature for 18 h. The mixture is neutralized with 20% HCl and extracted with diethyl ether. The organic layers are washed with saturated NaHCO3 solution, water, dried over MgSO4, filtered, concentrated by rotary evaporation and purified by flash chromatography to yield the desired compound. Structure is confirmed my 1H and 13C NMR.

出典