Reacción #452439

Ecuación de reacción

1-naphthoyl chloride

3,7-dimethyl-1,6-octadien-3-yl acetate

Lithium diisopropylamide

→

desired product

3,7-dimethyl-1,6-octadien-3-yl 3-(α-naphthyl)-3-oxo-propionate

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrofitted with a magnetic stirrer
2. 2
   workup.ADDITIONinternal thermometer, argon inlet, and addition funnel
3. 3
   workup.ADDITIONthe resulting solution added to the flask over 45 min
4. 4
   workup.ADDITIONOnce addition
5. 5
   TemperaturaThe mixture is warmed to -20° C.
6. 6
   workup.STIRRINGstirred at that temperature for 18 h
7. 7
   TemperaturaAfter warming to 0° C.
8. 8
   Otrothe mixture is quenched with 20% HCl (53 mL)
9. 9
   workup.ADDITIONThe mixture is poured into a separatory funnel
10. 10
    workup.ADDITIONcontaining ether (150 mL) and water (250 mL)
11. 11
    ExtracciónThe aqueous layer is extracted with ether (150 mL)
12. 12
    LavadoThe combined organic layers are washed with saturated NaHCO3 solution (2×100 mL), water (2×150 mL) and brine (150 mL)
13. 13
    Secadodried over MgSO4
14. 14
    Filtraciónfiltered
15. 15
    OtroThe solvent is removed by rotary evaporation
16. 16
    Otroto give an oil
17. 17
    OtroThe oil is purified by column chromatography (elution with 2% ethyl acetate/petroleum ether)
18. 18
    Otroto yield a colorless oil

Procedimiento

Lithium diisopropylamide (96.3 mL of a 2.0 M solution, 0.193 mol) is placed into a 500 mL three-necked round-bottomed flask fitted with a magnetic stirrer, internal thermometer, argon inlet, and addition funnel. The flask is cooled to -78° C. 3,7-dimethyl-1,6-octadien-3-yl acetate (17.81 g, 0.091 mol) is dissolved in THF (5 mL) and the resulting solution added to the flask over 45 min. Once addition is complete, the mixture is stirred for an additional 15 min. before being treated with a solution of 1-naphthoyl chloride (16.82 g, 0.086 mol) dissolved in THF (25 mL) over 30 min. The mixture is warmed to -20° C. and stirred at that temperature for 18 h. After warming to 0° C., the mixture is quenched with 20% HCl (53 mL). The mixture is poured into a separatory funnel containing ether (150 mL) and water (250 mL). The aqueous layer is extracted with ether (150 mL). The combined organic layers are washed with saturated NaHCO3 solution (2×100 mL), water (2×150 mL) and brine (150 mL), dried over MgSO4 and filtered. The solvent is removed by rotary evaporation to give an oil. The oil is purified by column chromatography (elution with 2% ethyl acetate/petroleum ether) to yield a colorless oil having 1H and 13C NMR spectra consistent with the desired product.

Fuente