n-Butyl lithium → HCID 3087422, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3.53 g of 2-oxo-5-isopropyloxy pyrrolidine in 85 cm3 of anhydrous tetrahydrofuran, cooled to -10° C., 15.42 g of a 1.6M solution of N-butyllithium in hexane is added, operating at -10° to -5° C. This is agitated for 30 minutes, while cooling to -45° C., then a solution of 5 g of styrenesulphonyl chloride (CA 47, 3262c, 1953) in 35 cm3 of anhydrous tetrahydrofuran is added slowly, while operating at -45° to -40° C. After allowing a return to ambient temperature, the solvent is evaporated off under reduced pressure and the residue is chromatographed on silica, eluting with a mixture of ethyl ethyl acetate and hexane (1--1). The product obtained is crystallized from ethanol, and 3.1 g of the expected product is obtained. m.p. 92°-94° C.

Provenance & Evidence