Dimethylformamide → 2-Chloro-4-Methyl thiazole-5-carbaldehyde

Temperature

-70 °C

To a stirred solution of 2-chloro-4-methylthiazole (0.3 g) in tetrahydrofuran (3 ml) was added a solution of n-butyllithium in n-hexane (1.63M, 1.52 ml) dropwise at −70° C. under a nitrogen atmosphere, and the mixture was stirred for 20 minutes at −70° C. To the resultant mixture was added N,N-dimethylformamide (0.21 ml) at −70° C., and the mixture was stirred for 40 minutes. The mixture was poured into a saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and evaporated. The residue was purified by column chromatography (silica gel 10 g, n-hexane:ethyl acetate=10:1) to give 2-chloro-5-formyl-4-methylthiazole (231 mg).

1. stirringthe mixture was stirred for 40 minutes
2. extractionextracted with ethyl acetate
3. washThe organic layer was washed with brine
4. dry with materialdried over magnesium sulfate
5. customevaporated
6. customThe residue was purified by column chromatography (silica gel 10 g, n-hexane:ethyl acetate=10:1)

ORD record

ord-b9267ffdec694c98b27378b4561cd067

Source dataset

uspto-grants-2003_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06521643B1