Trifluoroacetic acid → HCID 22933600, compound

HRID 1269967Notes

Reaction equation

HRID 1269967 reaction equation
O1CCCC1.[CH2:6]([C:8]1[C:16]([O:17]C2CCCCO2)=[CH:15][CH:14]=[C:13]2[C:9]=1[CH:10]=[N:11][N:12]2C1CCCCO1)[CH3:7].FC(F)(F)C(O)=O.[OH-].[Na+]>O>[CH2:6]([C:8]1[C:16]([OH:17])=[CH:15][CH:14]=[C:13]2[C:9]=1[CH:10]=[N:11][NH:12]2)[CH3:7]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 69436371HCID 69436371, compound

Product 1

HCID 22933600HCID 22933600, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a mixed solvent of tetrahydrofuran (5.0 ml) and water (2.5 ml) was suspended 4-ethyl-1-tetrahydro-2H-pyran-2-yl-5-(tetrahydro-2H-pyran-2-yloxy)-1H-indazole (1.40 g), followed by adding thereto trifluoroacetic acid (10.0 ml), and the resulting mixture was stirred for 2.5 hours while being maintained at room temperature. The reaction mixture was neutralized with a 2N-aqueous sodium hydroxide solution and extracted with ethyl acetate, and the extract solution was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain a crude product. The crude product was purified by a silica gel column chromatography (eluent: chloroform/ethyl acetate) to obtain 4-ethyl-1H-indazol-5-ol (314 mg, 47%) as a white solid.

Workup

  1. additionby adding
  2. extractionextracted with ethyl acetate
  3. dry with materialthe extract solution was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customto obtain a crude product
  7. customThe crude product was purified by a silica gel column chromatography (eluent: chloroform/ethyl acetate)

Sources & evidence

ORD record
ord-f1f673366b934e87b0ca7ef5287d9ff1
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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