Perchloric Acid → (7-methyl-1H-indazol-5-yl)-acetaldehyde

HRID 2099735

Reaktionsgleichung

Reaktionsgleichung von HRID 2099735
C[O:2][CH:3]=[CH:4][C:5]1[CH:6]=[C:7]2[C:11](=[C:12]([CH3:14])[CH:13]=1)[NH:10][N:9]=[CH:8]2.Cl(O)(=O)(=O)=O>O1CCCC1.O.C(OCC)(=O)C>[CH3:14][C:12]1[CH:13]=[C:5]([CH2:4][CH:3]=[O:2])[CH:6]=[C:7]2[C:11]=1[NH:10][N:9]=[CH:8]2

Komponenten

6

Edukt 2

HCID 24247Perchloric Acid2×HCID 690713565-(2-methoxy-vinyl)-7-methyl-1H-indazole

Produkt 1

HCID 57794606(7-methyl-1H-indazol-5-yl)-acetaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 5-(2-methoxy-vinyl)-7-methyl-1H-indazole (365 mg, 1.94 mmol, 1.0 equiv.) in tetrahydrofuran (8 mL) was added 60% perchloric acid (0.63 mL, 3 equiv) in one portion under nitrogen. After 2 h, more perchloric acid (0.63 mL) was added. After 4 h, LCMS indicated that no starting material was present. The reaction mixture was diluted with water and ethyl acetate. The layers were separated and the organic layer was washed with water (3×). The organic layer was separated, dried over sodium sulfate and concentrated in vacuo to give an off-white solid. The crude material was carried on without further purification. MS (ESI) [M+H]+=175.

Aufarbeitung

  1. waitAfter 4 h
  2. customThe layers were separated
  3. washthe organic layer was washed with water (3×)
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto give an off-white solid
  8. customThe crude material was carried on without further purification

Quellen und Nachweise

ORD-Eintrag
ord-ecfc209e6f2d414c95bff7906908e453
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07569578B2

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