Allyl-cis-2-octalone

To a solution of Al,9-2-octalone (2 mmol) in dichloromethane (3 ml) was added TiCl4 (2 mmol) dropwise. After 5 min, the solution was cooled to -78°C, and allyltrimethylsilane (2.8mmol) in dichloromethane (3ml) was added dropwise. After stirring for 18h at -78°C, and 5 h at -30°C, water was added to the mixture, which was then extracted thoroughly with ether. The combined organic extracts were washed with water, dried and concentrated. Distillation of the residue gave 9-allyl-cis-2-octalone (85%), b.p. 120°C/5 mmHg. 

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