Sodium Hypochlorite → Methyl 3-chloro-1-methyl-1H-pyrazole-5-carboxylate

HRID 402485

Reaktionsgleichung

Reaktionsgleichung von HRID 402485
[Cl:1][C:2]1[CH2:6][CH:5]([C:7]([O:9][CH3:10])=[O:8])[N:4]([CH3:11])[N:3]=1.Cl[O-].[Na+]>>[Cl:1][C:2]1[CH:6]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[N:4]([CH3:11])[N:3]=1

Komponenten

3

Edukt 2

HCID 23665760Sodium HypochloriteHCID 67209560methyl 3-chloro-1-methyl-4,5-dihydro-1H-pyrazole-5-carboxylate

Produkt 1

HCID 67209478Methyl 3-chloro-1-methyl-1H-pyrazole-5-carboxylateAusbeute 29 %

Versuchsvorschrift

Methyl 3-chloro-1-methyl-4,5-dihydro-1H-pyrazole-5-carboxylate (21 g, 119 mmol) was added drop wise to sodium hypochlorite (95 ml, 155 mmol) under ice cooling. Then, the ice bath was removed and stirring continued for 72 h. The organic phase was separated, washed with Na2S2O3 (10% aqueous solution) and water, dried over Na2SO4 and the solvent removed under reduced pressure. The resulting oil was purified by distillation (bp 35° C., 0.2 mbar) followed by column chromatography (eluent 80% hexane in EtOAc) to yield 6.0 g (29%) of the title compound. [1H-NMR (DMSO-d6, 360 MHz) δ 6.96 (s, 1H), 6.80 (s, 1H), 4.07 (s, 3H), 3.86 (s, 3H)]

Aufarbeitung

  1. customThen, the ice bath was removed
  2. customThe organic phase was separated
  3. washwashed with Na2S2O3 (10% aqueous solution) and water
  4. dry with materialdried over Na2SO4
  5. customthe solvent removed under reduced pressure
  6. distillationThe resulting oil was purified by distillation (bp 35° C., 0.2 mbar)

Quellen und Nachweise

ORD-Eintrag
ord-d78d5c7e05f141409e00285f612019ff
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08742106B2

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