Water → HCID 15501724, compound

Participants

Reaction Steps

In a dry 500 mL three-necked flask with a magnetic stirrer, a solution of 62.5 mL of n-butyllithium (1.6 M in n-hexane; 100 mmol) was added under a dry nitrogen atmosphere to a solution of 19.2 g (100 mmol) of triisopropyl-cyclopentadiene in 250 mL of tetrahydrofuran at -60° C. After heating to room temperature (in approximately one hour) stirring continued for a further two hours. After cooling to -60° C., a solution of dimethylaminoethyl tosylate (105 mmol) prepared in situ was added over a period of 5 minutes. The reaction mixture was heated to room temperature, followed by overnight stirring. After addition of water, the product was extracted with petroleum ether (40-60° C.). The combined organic layer was dried with sodium sulphate, and evaporated under reduced pressure. The conversion was greater than 95%. The yield of product after distillation (based on triisopropyl-cyclopentadiene) was approximately 55%.

Provenance & Evidence