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 tri-(2-propyl)cyclopentadiene in 250 mL of THF at -60° C. After heating 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 heated to room temperature, followed by overnight stirring. The degree of conversion of the reaction was monitored by GC. 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%. 30% of the product is geminally substituted.

Provenance & Evidence