反应详情

To a solution of 3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)benzoic acid (195 mg, 6.76 mmol) in chloroform (15 mL) were added oxalyl chloride (0.5 mL) and DMF in a catalytic amount. The reaction mixture was stirred for 30 minutes at room temperature, and the solvent was distilled off under reduced pressure. The residue was dissolved in anhydrous THF (20 mL), and 5-hydroxy-1-methylpyrazole hydrochloride (136 mg, 1.01 mmol), triethylamine (136 mg) and N,N-dimethylaminopyridine (250 mg) were added, followed by reflux with heating for 1 hour. The reaction mixture was allowed to cool to room temperature, and diluted with ethyl acetate (200 mL). The mixture was washed twice with a saturated brine. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was dissolved in anhydrous acetonitrile (10 mL), and triethylamine (136 mg) and acetone cyanohydrin in a catalytic amount were added. The mixture was stirred for 12 hours at room temperature. The solvent was distilled off under reduced pressure to obtain crude 5-hydroxy-1-methylpyrazol-4-yl 3-(2-methoxyethoxy)-2-methyl-4-(methylsulfonyl)phenyl ketone.

1. distillationthe solvent was distilled off under reduced pressure
2. dissolutionThe residue was dissolved in anhydrous THF (20 mL)
3. temperatureby reflux
4. temperaturewith heating for 1 hour
5. temperatureto cool to room temperature
6. washThe mixture was washed twice with a saturated brine
7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
8. distillationthe solvent was distilled off under reduced pressure
9. dissolutionThe residue was dissolved in anhydrous acetonitrile (10 mL)
10. additiontriethylamine (136 mg) and acetone cyanohydrin in a catalytic amount were added
11. stirringThe mixture was stirred for 12 hours at room temperature
12. distillationThe solvent was distilled off under reduced pressure