Hydrochloric Acid → 3-(4-Bromobutyl)-2,5,5-trimethyl-4-thiazolidinone

Participants

Reaction Conditions

Reaction Steps

To a -73° C. solution of 3-(4-bromobutyl)-2-methyl-4-thiazolidinone (6.00 g), methyliodide (10.99 g) and THF (50 ml) under nitrogen was added lithium bis(trimethylsilyl)amide (0.0500 mol) in THF (50 ml) at a rate to maintain the internal temperature below -55° C. The resulting solution was stirred at <-55° C. for 10 minutes, allowed to warm to -40° C., and at which temperature 1N HCl (250 ml) was added. The aqueous mixture was extracted with 25% benzene/ether (3×125 ml). The combined extracts were washed with brine (200 ml), dried (Na2SO4), and concentrated to a liquid which was chromatographed on silica gel yielding 5.07 g of a liquid. The liquid was distilled to give 3.80 g of a clear liquid, b.p. 109°-114° C. at 0.20 mmHg.

Provenance & Evidence