Tetrapropylammonium → 1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carbaldehyde

HRID 2111909Notes

Reaction equation

HRID 2111909 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([CH2:7][OH:8])[C:4]([C:9]([F:12])([F:11])[F:10])=[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]([C:9]([F:10])([F:11])[F:12])=[N:3]1

Participants

4

Reactant 3

HCID 9559TetrapropylammoniumHCID 82029Methyl morpholine oxideHCID 21039553(1-Methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl)methanol

Product 1

HCID 533020711-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carbaldehydeYield 88%

Procedure

To a solution of 1-methyl-3-trifluoromethyl-1H-pyrazol-4-methanol (0.51 g, 2.83 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 (15 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-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxaldehyde (0.44 g, 88%), which is used without further purification. 1H NMR (CDCl3): δ=9.92 (1H, s), 7.99 (1H, s), 4.00 (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-6342d96a9299461fa7d52d15ce255568
Source dataset
uspto-grants-2009_04
Patent number
US07521462B2

Reaction notes

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