Tetrapropylammonium → 1,3-dimethyl-1H-pyrazole-4-carbaldehyde

HRID 2111907Notes

Reaction equation

HRID 2111907 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([CH2:7][OH:8])[C:4]([CH3:9])=[N:3]1.C[N+]1([O-])CCOCC1.C([N+](CCC)(CCC)CCC)CC>>[CH3:1][N:2]1[CH:6]=[C:5]([CH:7]=[O:8])[C:4]([CH3:9])=[N:3]1

Participants

4

Reactant 3

HCID 9559TetrapropylammoniumHCID 82029Methyl morpholine oxideHCID 949772(1,3-dimethyl-1H-pyrazol-4-yl)methanol

Product 1

HCID 8472851,3-dimethyl-1H-pyrazole-4-carbaldehydeYield 81%

Procedure

To a solution of 1,3-dimethyl-1H-pyrazol-4-methanol (0.33 g, 2.63 mmol), N-methyl morpholine N-oxide (0.37 g, 3.16 mmol), and crushed, dried, and activated 4 Å sieves (1.5 g) in anhydrous dichloromethane (20 ml), is added tetrapropyl ammonium peruthenate (0.09 g, 0.26 mmol). The reaction mixture is stirred for one hour at room temperature, then filtered through a silica gel plug and eluted with ethyl acetate. The filtrate is concentrated in vacuo to give 1,3-dimethyl-1H-pyrazole-4-carboxaldehyde (0.26 g, 81%) which is used without further purification. 1H NMR (CDCl3): δ=9.83 (1H, s), 7.78 (1H, s), 3.86 (3H, s), 2.46 (3H, s).

Workup

  1. customdried
  2. filtrationfiltered through a silica gel plug
  3. washeluted with ethyl acetate
  4. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-1aed39ac6cba41d79fb645ea453960e9
Source dataset
uspto-grants-2009_04
Patent number
US07521462B2

Reaction notes

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