Perchloric Acid → HCID 90092728, compound

HRID 1774557Notes

Reaction equation

HRID 1774557 reaction equation
[CH3:1][C:2]1([CH3:26])[CH2:7][CH2:6][C:5]([C:8]2[C:9]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:10][N:11]([CH3:19])[C:12]=2[CH:13]([OH:18])[C:14]([O:16][CH3:17])=[O:15])=[CH:4][CH2:3]1.Cl(O)(=O)(=O)=O>C(OC(C)(C)C)(=O)C>[C:2]([O:18][CH:13]([C:12]1[N:11]([CH3:19])[N:10]=[C:9]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:8]=1[C:5]1[CH2:6][CH2:7][C:2]([CH3:26])([CH3:1])[CH2:3][CH:4]=1)[C:14]([O:16][CH3:17])=[O:15])([CH3:7])([CH3:3])[CH3:1]

Participants

4

Reactant 2

HCID 24247Perchloric AcidHCID 90092984HCID 90092984, compound

Product 1

HCID 90092728HCID 90092728, compoundYield 152.6%

Reagents, catalysts & solvents 1

HCID 10908tert-Butyl acetateSolvent

Procedure

To a solution of methyl 2-[4-(4,4-dimethylcyclohex-1-en-1-yl)-1-methyl-3-phenyl-1H-pyrazol-5-yl]-2-hydroxyacetate (1e) (135 mg, 0.38 mmol) in tert-butyl acetate (7 mL) at 0° C. was added perchloric acid (0.87 mL). The mixture was stirred for 80 minutes at room temperature before being slowly quenched with a saturated solution of potassium carbonate (20 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (2×30 mL). The organic layers were dried over sodium sulfate and concentrated in vacuo. The residue was purified by preparative TLC (cyclohexane/ethyl acetate 80/20) to provide methyl 2-(tert-butoxy)-2-[4-(4,4-dimethylcyclohex-1-en-1-yl)-1-methyl-3-phenyl-1H-pyrazol-5-yl]acetate (1f) (121 mg, 0.29 mmol, 77%) as a clear yellow oil.

Workup

  1. custombefore being slowly quenched with a saturated solution of potassium carbonate (20 mL)
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate (2×30 mL)
  4. dry with materialThe organic layers were dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by preparative TLC (cyclohexane/ethyl acetate 80/20)

Sources & evidence

ORD record
ord-abe477a5e5cb49d3817f8aa519e7ace9
Source dataset
uspto-grants-2016_02
Patent number
US09260395B2

Reaction notes

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