Reacción #452445

Ecuación de reacción

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

Disolventes

tetrahydrofuran

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrofitted 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
   Extracciónextracted with diethyl ether
8. 8
   LavadoThe organic layers are washed with saturated NaHCO3 solution, water
9. 9
   Secadodried over MgSO4
10. 10
    Filtraciónfiltered
11. 11
    Concentraciónconcentrated by rotary evaporation
12. 12
    Otropurified by flash chromatography

Procedimiento

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.

Fuente