4-Toluenesulfonyl chloride → HCID 54408321, compound

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Reaction Conditions

Reaction Steps

To a flask containing 10.36 g of 5-hexene-1-ol, 24.11 g of p-toluenesulfonyl chloride and 200 mL of diethylether were added and well mixed. The solution was cooled down to −10° C., and 353.5 g of well ground KOH was slowly added for 10 min to the solution. The solution was stirred for 30 minutes at −15˜5° C. The solution was then poured to 200 mL of ice-water. Ether solution was separated with a funnel. Then the ether solution was dried with anhydrous MgSO4, filtered, and then ether was removed from the filtrate under reduced pressure. The remained product was clear and sticky. This product was dissolved in 120 mL of anhydrous THF. This solution was cooled down to 0° C. and 65 mL of 2N THF solution of NaCp was added to the cold solution. This solution was stirred for about 3˜5 hours, and mixed with 200 mL of water and 200 mL of hexane in a separatory funnel. The organic layer was extracted and dried by MgSO4 and filtered. Slightly yellow filtrate was vacuum dried in 0.2 torr at 55° C. to produce 9.643 g of product, pure Hexenylcyclopentadiene (Yield: 65%). This compound, 9.643 g, was dissolved in 100 mL of THF and cooled down to −78° C. using dry ice/aceton slush. To this solution, 26 mL of nBuLi (2.5M, hexane) was added and the solution was stirred overnight with a slow warming to room temperature. This solution was then added to a flask containing 0.5 equivalent of ZrCl4(THF)2 at 55° C. and was agitated for 3 days. The solvent was removed under reduced pressure and 200 mL of hexane was added and heated. Filtration at 55° C. was followed by a removal of hexane and produced the white solid product (Yield: 65%). Spectroscopic analysis of the product by a NMR method is as follows:

Provenance & Evidence