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

HRID 532821Notes

Reaction equation

HRID 532821 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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+).

Workup

  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)

Sources & evidence

ORD record
ord-6e2088c455ce4ac4940d28fb918139ea
Source dataset
uspto-grants-2014_10
Patent number
US08853202B2

Reaction notes

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