反应详情

温度

10 °C

A solution of 6-[2,6-dichloro-4-(2-hydroxy-ethyl)-phenoxy]-4-isopropyl-2-methyl-pyridazin-3-one (36) (330 mg, 0.92 mmol) in acetone (5 mL) was treated with Jones Reagent (0.51 mL of a 2.7M solution,) slowly dropwise at 10° C. The resulting red reaction mixture was stirred at 10° C. for 30 min. The reaction mixture was then concentrated under vacuum. The resulting residue was diluted with ethyl acetate (25 mL) and water (20 mL) and was treated with sodium bisulfite (100 mg). The resulting mixture was shaken and turned from red to green. The aqueous layer was separated and was re-extracted with ethyl acetate (25 mL). The organic layers were combined and washed with a saturated aqueous sodium chloride solution. The organic layer was separated, dried with sodium sulfate, filtered, and concentrated under vacuum. The resulting solid was recrystallized from ethyl acetate and dried under vacuum overnight to afford [3,5-dichloro-4-(5-isopropyl-1-methyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-acetic acid (37) (70 mg, 19%) as a white solid; EI(+)-HRMS) m/z calcd for C16H16Cl2N2O4 (M+H)+ 371.0560, found 371.0561. Molecular Weight=371.2229; Exact Mass=370.0487

1. customslowly dropwise at 10° C
2. concentrationThe reaction mixture was then concentrated under vacuum
3. additionThe resulting residue was diluted with ethyl acetate (25 mL) and water (20 mL)
4. additionwas treated with sodium bisulfite (100 mg)
5. stirringThe resulting mixture was shaken
6. customThe aqueous layer was separated
7. extractionwas re-extracted with ethyl acetate (25 mL)
8. washwashed with a saturated aqueous sodium chloride solution
9. customThe organic layer was separated
10. dry with materialdried with sodium sulfate
11. filtrationfiltered
12. concentrationconcentrated under vacuum
13. customThe resulting solid was recrystallized from ethyl acetate
14. customdried under vacuum overnight