Hexane → 1-(5-Methyl-1,3-thiazol-2-yl)ethan-1-one

Temperature

-78 °C

Commercially available 5-methyl-1,3-thiazole (218 mg) was dissolved in tetrahydrofuran (5 ml) to prepare a solution which was then cooled to −78° C. A hexane solution (1.56 M) (1.4 ml) of n-butyllithium was slowly added to the cooled solution over a period of 10 min, and the mixture was stirred at −78° C. for 2 hr. N-Methoxy-N-methylacetamide (206 mg) was dissolved in tetrahydrofuran (2 ml) to prepare a solution which was then slowly added thereto over a period of 10 min, followed by stirring at −78° C. for 2 hr. The cooling bath was removed, an aqueous saturated ammonium chloride solution (5 ml) was added, and the mixture was stirred for 30 min. Further, water (5 ml) was added thereto, 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 (267 mg, 86%).

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

ORD record

ord-a79f756b58cf4e4fab1d8a38f3565db4

Source dataset

uspto-grants-2009_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07598258B2