Tert-Butyl nitrite → Methyl 5-methyl-1,3-thiazole-4-carboxylate

To a solution of methyl 2-amino-5-methyl-1,3-thiazole-4-carboxylate (2.15 g, 12.5 mmol) in tetrahydrofuran (60 mL) was slowly added tert-butyl nitrite (2.23 mL, 18.7 mmol) with stirring at 50° C., and the mixture was stirred at 60° C. for 2 hr. The mixture was diluted with water (100 mL), and extracted with ethyl acetate (100 mL×2). The organic layer was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20→0/100) to give the title compound (1.17 g, yield 60%).

1. stirringthe mixture was stirred at 60° C. for 2 hr
2. extractionextracted with ethyl acetate (100 mL×2)
3. concentrationThe organic layer was concentrated under reduced pressure
4. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=80/20→0/100)

ORD-Eintrag

ord-02012051ffb148db8b7de8193bc052e3

Quelldatensatz

uspto-grants-2011_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08044049B2