Hexane → 2-Acetyl-4,5-dimethylthiazole

Temperature

-78 °C

Commercially available 4,5-dimethyl-1,3-thiazole (453 mg) was dissolved in tetrahydrofuran (10 ml) to prepare a solution which was then cooled to −78° C. A hexane solution (1.56 M) (2.8 ml) of n-butyllithium was slowly added over a period of 10 min, and the mixture was stirred at −78° C. for 2 hr. N-Methoxy-N-methylacetamide (454 mg) was dissolved in tetrahydrofuran (2 ml) to prepare a solution which was then slowly added over a period of 10 min, and the mixture was stirred at −78° C. for 2 hr. The cooling bath was removed, an aqueous saturated ammonium chloride solution (10 ml) was added, and the mixture was stirred for 30 min. Further, water (10 ml) was added, and the reaction solution was extracted with ethyl acetate. The organic layer was washed with saturated brine and was dried over sodium sulfate. The solvent was removed, and the residue was purified by chromatography on silica gel using hexane/ethyl acetate for development to give the title compound (609 mg, 98%).

1. customto prepare a solution which
2. customto prepare a solution which
3. additionwas then slowly added over a period of 10 min
4. stirringthe mixture was stirred at −78° C. for 2 hr
5. customThe cooling bath was removed
6. additionan aqueous saturated ammonium chloride solution (10 ml) was added
7. stirringthe mixture was stirred for 30 min
8. additionFurther, water (10 ml) was added
9. extractionthe reaction solution was extracted with ethyl acetate
10. washThe organic layer was washed with saturated brine
11. dry with materialwas dried over sodium sulfate
12. customThe solvent was removed
13. customthe residue was purified by chromatography on silica gel

ORD record

ord-a4f712416d0447db95b3e818417207ee

Source dataset

uspto-grants-2009_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07598258B2