4-Toluenesulfonyl chloride → HCID 131721810, compound

Participants

Reaction Conditions

Reaction Steps

In a Schlenk vessel, to a solution of cyclohexyldiisopropylcyclopentadiene (9.28 g; 40.0 mmol) in dry THF (150 mL) at room temperature, a solution of n-butyllithium in hexane (25.0 mL; 1.6 mol/L; 40.0 mmol) was added dropwise. Then, in another Schlenk vessel, a solution of n-butyllithium in hexane (25.0 mL; 1.6 mol/L; 40.0 mmol) was added dropwise to a cold (-78° C.) solution of dimethylaminoethanol (3.56 g; 40.0 mmol) in THF (100 mL). After an hour and a half's stirring at room temperature, the mixture was again cooled to -78° C. and the solid tosyl chloride (8.10 g; 40.0 mmol) was added slowly. The mixture was brought to 0° C., being stirred for 5 minutes in the process, again cooled to -78° C., and the mixture from the first Schlenk vessel then added at once. After 16 hours' stirring at room temperature the conversion was 100%. After column chromatography 11.1 g of cyclohexyl(dimethylaminoethyl)-di-(2-propyl)cyclopentadiene were obtained.

Provenance & Evidence