4-Methyl-1,3-thiazole-2-carbaldehyde → 7586-99-4

To a solution of 4-methylthiazole-2-carbaldehyde of preparation 94 (5.8 g, 45.6 mmol) in anhydrous THF (100 mL) was added a THF solution of MeMgBr (3M, 30.4 mL, 91.3 mmol) drop-wise at −60° C. under N2, and the mixture was warmed to room temperature and stirred for another 2 hours. TLC (petroleum ether:EtOAc 2:1) showed the reaction was completed. The mixture was quenched by saturated NH4Cl solution (120 mL), and extracted with EtOAc (100 mL×3). The combined organic extracts were washed with brine (50 mL), dried over sodium sulfate and concentrated in vacuum to give the residue which was purified by a silica gel column eluting with petroleum ether:EtOAc=20:1-8:1 to give the title compound as a yellow oil (3.4 g, 50%).

1. customThe mixture was quenched by saturated NH4Cl solution (120 mL)
2. extractionextracted with EtOAc (100 mL×3)
3. washThe combined organic extracts were washed with brine (50 mL)
4. dry with materialdried over sodium sulfate
5. concentrationconcentrated in vacuum
6. customto give the residue which
7. customwas purified by a silica gel column
8. washeluting with petroleum ether

ORD record

ord-f3e5a35a0c25443d9a9728b6fc78f77f

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08916593B2