Hydrochloric Acid → HCID 89962986, compound

HRID 337819Notes

Reaction equation

HRID 337819 reaction equation
[CH3:1][C:2]1([CH3:18])[CH2:11][CH2:10][C:5]2(OCC[O:6]2)[C:4]([C:12]2[N:16]([CH3:17])[N:15]=[CH:14][CH:13]=2)=[CH:3]1.Cl.[OH-].[Na+]>C1COCC1>[CH3:1][C:2]1([CH3:18])[CH2:11][CH2:10][C:5](=[O:6])[C:4]([C:12]2[N:16]([CH3:17])[N:15]=[CH:14][CH:13]=2)=[CH:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 89962934HCID 89962934, compound

Product 1

HCID 89962986HCID 89962986, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the 5-(8,8-dimethyl-1,4-dioxaspiro[4.5]dec-6-en-6-yl)-1-methyl-1H-pyrazole (580 mg, 2.34 mmol) prepared in Example 67b and 2 M hydrochloric acid (2.0 mL) in THF (5.0 mL) was stirred for 1 hour under reflux. After allowing to cool, a 1 M aqueous sodium hydroxide solution (5.0 mL) was added to the reaction solution, followed by extraction with ethyl acetate (50 mL). The thus obtained organic layer was dried over anhydrous sodium sulfate. After vacuum concentration, the residue was purified with silica gel chromatography (hexane/ethyl acetate=1:1) to yield the title compound (432 mg, 91%) as a colorless oil.

Workup

  1. temperatureunder reflux
  2. temperatureto cool
  3. extractionfollowed by extraction with ethyl acetate (50 mL)
  4. dry with materialThe thus obtained organic layer was dried over anhydrous sodium sulfate
  5. concentrationAfter vacuum concentration
  6. customthe residue was purified with silica gel chromatography (hexane/ethyl acetate=1:1)

Sources & evidence

ORD record
ord-ebba767d7a8a4dbf8fd3cb881f9c2e5c
Source dataset
uspto-grants-2014_11
Patent number
US08889741B2

Reaction notes

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