Nitrogen → 1-[5-(4-Nitro-pyrazol-1-ylmethyl)-furan-2-yl]-ethanone

HRID 2064918Notes

Reaction equation

HRID 2064918 reaction equation
N#N.[N+:3]([C:6]1[CH:7]=[N:8][N:9]([CH2:11][C:12]2[O:16][C:15]([CH:17]([OH:19])[CH3:18])=[CH:14][CH:13]=2)[CH:10]=1)([O-:5])=[O:4]>C(C#N)(C)=O.O=[Mn]=O>[N+:3]([C:6]1[CH:7]=[N:8][N:9]([CH2:11][C:12]2[O:16][C:15]([C:17](=[O:19])[CH3:18])=[CH:14][CH:13]=2)[CH:10]=1)([O-:5])=[O:4]

Participants

5

Reactant 2

HCID 947NitrogenHCID 669281261-[5-(4-Nitro-pyrazol-1-ylmethyl)-furan-2-yl]-ethanol

Product 1

HCID 669282261-[5-(4-Nitro-pyrazol-1-ylmethyl)-furan-2-yl]-ethanone

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 694302-OxopropiononitrileSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 1-[5-(4-nitro-pyrazol-1-ylmethyl)-furan-2-yl]-ethanol (4.94 g, 20.82 mmol) in AcCN (200.0 mL) was treated at rt with MnO2 (12.07 g, 124.90 mmol) and the reaction mixture was stirred at rt overnight before being filtered through Celite. The solvent was removed under reduced pressure. Purification of the residue by FC (50:00 hept-EA) gave the title compound as a yellow solid. TLC: rf (50:50 hept-EA)=0.26. LC-MS-conditions 02: tR=0.83 min. 1H NMR (400 MHz, CDCl3) δ 2.47 (s, 3H), 5.41 (s, 2H), 6.60 (d, J=3.3 Hz, 1H), 7.17 (d, J=3.3 Hz, 1H), 8.10 (s, 1H), 8.25 (s, 1H).

Workup

  1. filtrationbefore being filtered through Celite
  2. customThe solvent was removed under reduced pressure
  3. customPurification of the residue by FC (50:00 hept-EA)

Sources & evidence

ORD record
ord-f3d2efc5b3f94507bdb9895c5b15779d
Source dataset
uspto-grants-2012_10
Patent number
US08288419B2

Reaction notes

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