Reaktion #42170

Reaktionsgleichung

ammonium chloride

n-heptyl chloride

phenylmagnesium chloride

→

1-phenylheptane

Lösungsmittel

tetrahydrofuran

N-methylpyrrolidinone

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeA 30-ml four-necked flask was equipped with a stirrer
2. 2
   workup.ADDITIONadded into the flask
3. 3
   SonstigeThe flask was purged with argon
4. 4
   workup.STIRRINGby stirring at 25° C. for 30 minutes
5. 5
   workup.STIRRINGby stirring at 25° C. for 30 minutes
6. 6
   workup.STIRRINGby stirring at 25° C. for 19 hours
7. 7
   workup.ADDITIONwere added
8. 8
   Sonstigefollowed by separation
9. 9
   SonstigeThe organic phase was purified by column chromatography

Vorschrift

A 30-ml four-necked flask was equipped with a stirrer, a thermometer, a dropping funnel and a reflux condenser. 0.027 g (0.12 mmol) of palladium (II) acetate and 7 ml of N-methylpyrrolidinone were weighed in the flask, followed by stirring. Further, 0.079 g (0.12 mmol) of tricyclohexylphosphonium tetra-para-tolylborate obtained in Example B-16 was weighed in air and added into the flask. The flask was purged with argon, followed by stirring at 25° C. for 30 minutes. 0.404 g (3 mmol) of n-heptyl chloride was added, followed by stirring at 25° C. for 30 minutes. 2 ml (4.4 mmol) of 2.2M tetrahydrofuran solution of phenylmagnesium chloride was added dropwise at 25° C. over a period of 10 minutes, followed by stirring at 25° C. for 19 hours. After the completion of the reaction, 6 ml of tetrahydrofuran and 10 ml of saturated aqueous ammonium chloride solution were added, followed by separation. The organic phase was purified by column chromatography to afford 0.434 g of 1-phenylheptane (yield: 82 mol % based on n-heptyl chloride). The identification of the product was made by mass spectroscopy.

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