반응 #42173

반응 방정식

n-heptyl bromide

tetra-n-butylammonium fluoride

di-tert-butylmethylphosphonium tetraphenylborate

trimethoxyphenylsilane

→

1-phenylheptane

수율 85.1%

용매

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   기타A 30-ml four-necked flask was equipped with a stirrer
2. 2
   workup.ADDITIONadded into the flask
3. 3
   기타The flask was purged with argon
4. 4
   workup.STIRRINGby stirring at 25° C. for 21 hours
5. 5
   기타After the completion of the reaction, 5 ml of toluene and 10 ml of saturated sodium chloride solution
6. 6
   workup.ADDITIONwere added
7. 7
   기타followed by separation
8. 8
   기타The organic phase was purified by column chromatography

실험 절차

A 30-ml four-necked flask was equipped with a stirrer, a thermometer and a reflux condenser. 0.358 g (2 mmol) of n-heptyl bromide, 0.476 g (2.4 mmol) of trimethoxyphenylsilane, 0.021 g (0.08 mmol) of palladium (II) bromide, 4.8 ml (4.8 mmol) of 1M tetrahydrofuran solution of tetra-n-butylammonium fluoride and 4.8 ml of tetrahydrofuran were weighed in the flask, followed by stirring. Further, 0.096 g (0.2 mmol) of di-tert-butylmethylphosphonium tetraphenylborate obtained in Example B-1 was weighed in air and added into the flask. The flask was purged with argon, followed by stirring at 25° C. for 21 hours. After the completion of the reaction, 5 ml of toluene and 10 ml of saturated sodium chloride solution were added, followed by separation. The organic phase was purified by column chromatography to afford 0.300 g of 1-phenylheptane (yield: 85 mol % based on n-heptyl bromide). The identification of the product was made by mass spectroscopy.

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