Hydrochloric Acid → HCID 67091209, compound

Temperature

80 °C

To a round bottom flask containing (5-tert-Butyl-2-p-tolyl-2H-pyrazol-3-yl)-trimethylsilanyloxy-acetonitrile was added 100 mL concentrated HCl and heated to 80° C. After overnight heating, the reaction was diluted with 150 mL water and extracted with DCM (3×100 mL). The organic layers were washed with brine, dried over sodium sulfate, and concentrated under vacuum. The residue was then re-dissolved in about 75 mL methanol, followed by the addition of KOH (0.45 g, 8 mmol) and the solution was refluxed for 2 h. The reaction mixture was then cooled to room temperature, concentrated under vacuum. Several pieces of crushed ice were added to the flask with the reaction residue and acidified with 1N HCl. The mixture was then diluted with 100 mL water and extracted with DCM (3×100 mL). The organic layers were washed with brine, dried over MgSO4, and concentrated under vacuum to yield 0.35 g (60%) of the desired product. No further purification was attempted. Expected mass=288. Observed mass=289.

1. temperatureAfter overnight heating
2. extractionextracted with DCM (3×100 mL)
3. washThe organic layers were washed with brine
4. dry with materialdried over sodium sulfate
5. concentrationconcentrated under vacuum
6. dissolutionThe residue was then re-dissolved in about 75 mL methanol
7. temperaturethe solution was refluxed for 2 h
8. temperatureThe reaction mixture was then cooled to room temperature
9. concentrationconcentrated under vacuum
10. additionSeveral pieces of crushed ice were added to the flask with the reaction residue
11. additionThe mixture was then diluted with 100 mL water
12. extractionextracted with DCM (3×100 mL)
13. washThe organic layers were washed with brine
14. dry with materialdried over MgSO4
15. concentrationconcentrated under vacuum

ORD record

ord-de1c4a4d3f3b4b13af0ded48965eb12c

Source dataset

uspto-grants-2010_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07749999B2