Potassium Hydroxide → 4-ethoxy-1-(4-fluorophenyl)-1H-pyrazole-3-carboxylic acid

HRID 1465185Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1465185
[CH2:1]([O:3][C:4]1[C:5]([C:16]([O:18]CC)=[O:17])=[N:6][N:7]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[CH:8]=1)[CH3:2].[OH-].[K+]>CCO.C(Cl)Cl.O>[CH2:1]([O:3][C:4]1[C:5]([C:16]([OH:18])=[O:17])=[N:6][N:7]([C:9]2[CH:10]=[CH:11][C:12]([F:15])=[CH:13][CH:14]=2)[CH:8]=1)[CH3:2]

Komponenten

6

Edukt 2

HCID 14797Potassium HydroxideHCID 66611816Ethyl 4-ethoxy-1-(4-fluorophenyl)pyrazole-3-carboxylate

Produkt 1

HCID 336766774-ethoxy-1-(4-fluorophenyl)-1H-pyrazole-3-carboxylic acidAusbeute 93,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

D2 (38 mmol, 1.0 eq.) and aq. KOH-solution (3M, 190 mmol, 5.0 eq.) in EtOH (152 mL) were heated for 45 min at 50° C. The mixture was cooled to RT and diluted with DCM and water. The aq. phase was washed a second time with DCM. The aq. phase was acidified with aq. HCl-solution (1N) to pH=1 and extracted with EtOAc. The combined organic phase was washed with brine and dried over Na2SO4. Removal of the solvent yielded the product D3 as a brown solid (8.88 g, 93% over 2 steps). 1H NMR (400 MHz, d6-DMSO, 300K) δ 1.34 (t, J=7.0 Hz, 3H), 4.02 (q, J=7.0 Hz, 2H), 7.37 (dd, J=J=9.0 Hz, 2H), 7.87 (dd, J=9.0 Hz, J=4.6 Hz, 2H), 8.38 (s, 1H), 12.68 (br s, 1H). MS (ES) C12H11FN2O3 requires: 250. Found: 251 (M+H)+ and 273 (M+Na)+.

Aufarbeitung

  1. washThe aq. phase was washed a second time with DCM
  2. extractionextracted with EtOAc
  3. washThe combined organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. customRemoval of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-2e8ef89d5a6748dfaad9542f25ba378c
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US08999982B2

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