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 (1.6M in n-hexane; 100 mmol) was added under a dry nitrogen atmosphere to a solution of 19.2 g (100 mmol) of triisopropylcyclopentadiene in 250 mL of THF at -60° C. After warming to room temperature (in approximately 1 hour) stirring continued for a further 2 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 warmed 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 (Na2SO4) and evaporated under reduced pressure. The conversion was greater than 95%. The yield of product after distillation (based on triisopropylcyclopentadiene) was approximately 55%.

Provenance & Evidence