Ethyl Acetate → 1-(1-Phenyl-1H-pyrazol-3-yl)-propan-1-one

HRID 2063547Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2063547
[C:1]1([N:7]2[CH:11]=[CH:10][C:9]([CH:12]([OH:15])[CH2:13][CH3:14])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.CCOC(C)=O>C(Cl)Cl>[C:1]1([N:7]2[CH:11]=[CH:10][C:9]([C:12](=[O:15])[CH2:13][CH3:14])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 159087Triacetoxyperiodinane2×HCID 593661741-(1-Phenyl-1H-pyrazol-3-yl)-propan-1-ol

Produkt 1

HCID 593661871-(1-Phenyl-1H-pyrazol-3-yl)-propan-1-oneAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

1-(1-Phenyl-1H-pyrazol-3-yl)-propan-1-ol (631 mg, 3.12 mmol) was dissolved in CH2Cl2 (16 mL) and Dess-Martin periodinane (1.6 g, 3.8 mmol) was added in one portion. After 40 minutes, TLC (2:1 hexanes:EtOAc) indicated a mixture of starting material and product. Additional Dess-Martin periodinane (800 mg, 1.88 mmol) was added and the mixture was stirred at ambient temperature. After 30 minutes, TLC indicated no further conversion to product. The reaction mixture was diluted with CH2Cl2 and washed with aqueous Na2S2O3 (1×) and saturated NaHCO3 (2×). The CH2Cl2 layer was dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography (2:1 hexanes:EtOAc) to provide the title compound as a colorless solid (487 mg, 78%). 1H NMR (400 MHz, CDCl3) δ 7.91 (d, 1H, J=2.4 Hz), 7.73 (d, 2H, J=8.8 Hz), 7.48 (t, 2H, J=7.2 Hz), 7.35 (t, 1H, J=7.6 Hz), 6.96 (d, 1H, J=2.8 Hz), 3.13 (q, 2H, J=7.2 Hz), 1.24 (t, 3H, J=7.2 Hz). MS (ES) m/z 201.0 (M+H+).

Aufarbeitung

  1. additiona mixture of starting material and product
  2. waitAfter 30 minutes
  3. washwashed with aqueous Na2S2O3 (1×) and saturated NaHCO3 (2×)
  4. dry with materialThe CH2Cl2 layer was dried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (2:1 hexanes:EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-b47cfaacb14e411493fe839c0696f090
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08288373B2

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