Reacción #42172

Ecuación de reacción

ammonium chloride

tetrahydrofuran

n-heptylmagnesium chloride

chlorobenzene

→

1-phenylheptane

Disolventes

N-methylpyrrolidinone

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroA 50-ml four-necked flask was equipped with a stirrer
2. 2
   OtroThe flask was purged with argon
3. 3
   workup.STIRRINGby stirring at 25° C. for 30 minutes
4. 4
   OtroThe reaction liquid
5. 5
   Otropreviously obtained
6. 6
   workup.ADDITIONwas added
7. 7
   workup.STIRRINGby stirring at 25° C. for 30 minutes
8. 8
   workup.STIRRINGby stirring at 120° C. for 16 hours
9. 9
   workup.ADDITIONwere added
10. 10
    Otrofollowed by separation
11. 11
    OtroThe organic phase was purified by column chromatography

Procedimiento

A 50-ml four-necked flask was equipped with a stirrer, a thermometer, a dropping funnel and a reflux condenser. 1.090 g (8 mmol) of zinc chloride and 4 ml of N-methylpyrrolidinone were weighed in the flask. The flask was purged with argon, followed by stirring. 3.5 ml (7 mmol) of 2M tetrahydrofuran solution of n-heptylmagnesium chloride was added dropwise at 25° C. over a period of 30 minutes, followed by stirring at 25° C. for 30 minutes. The reaction liquid previously obtained was added, followed by stirring at 25° C. for 30 minutes. Further, 0.558 g (5 mmol) of chlorobenzene was added, followed by stirring at 120° C. for 16 hours. After the completion of the reaction, 10 ml of toluene and 10 ml of saturated aqueous ammonium chloride solution were added, followed by separation. The organic phase was purified by column chromatography to afford 0.688 g of 1-phenylheptane (yield: 78 mol % based on chlorobenzene). The identification of the product was made by mass spectroscopy.

Fuente