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

HRID 2111909Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2111909
[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

Komponenten

4

Edukt 3

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

Produkt 1

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

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-6342d96a9299461fa7d52d15ce255568
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07521462B2

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