Hydrochloric Acid → HCID 10542663, compound

Temperature

-65 °C

To a solution of 3-(4-bromobutyl)-4-thiazolidinone (25 g) in tetrahydrofuran (350 ml) cooled to -60° C., was added 1,5-diiodopentane (100 g). The resulting slurry was allowed to cool to -65° C. and a solution of lithium bis(trimethylsilyl)amide in hexanes (220 ml) was added dropwise over a period of 30 minutes while maintaining the internal temperature at or below -55° C. The resulting mixture was stirred for 15 minutes and the internal temperature allowed to rise to 0° C. 0.5N HCl (500 ml) was added to quench the reaction and the mixture was concentrated in vacuo to remove the THF. The aqueous mixture was extracted twice with 250 ml portions of ether, washed with water (400 ml) and brine (400 ml), dried (Na2SO4) and concentrated to a liquid. The liquid was chromatographed on silica gel (elution with 20% ethyl acetate/hexane) to give a liquid.

1. temperaturewhile maintaining the internal temperature at or below -55° C
2. customto rise to 0° C
3. customto quench
4. customthe reaction
5. concentrationthe mixture was concentrated in vacuo
6. customto remove the THF
7. extractionThe aqueous mixture was extracted twice with 250 ml portions of ether
8. washwashed with water (400 ml) and brine (400 ml)
9. dry with materialdried (Na2SO4)
10. concentrationconcentrated to a liquid
11. customThe liquid was chromatographed on silica gel (elution with 20% ethyl acetate/hexane)
12. customto give a liquid

ORD record

ord-25c38c6168934a1ba3413730e9f7e3da

Source dataset

uspto-grants-1991_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05041445