Pyrazole → methyl 2-(benzyloxy)-4-(1H-pyrazol-1-yl)benzoate

HRID 454472

Reaktionsgleichung

Reaktionsgleichung von HRID 454472
[NH:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.N1CCC[C@@H]1C(O)=O.C(=O)([O-])[O-].[K+].[K+].[CH2:20]([O:27][C:28]1[CH:37]=[C:36](I)[CH:35]=[CH:34][C:29]=1[C:30]([O:32][CH3:33])=[O:31])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>[Cu]I.C(OCC)(=O)C.O.CS(C)=O>[CH2:20]([O:27][C:28]1[CH:37]=[C:36]([N:1]2[CH:5]=[CH:4][CH:3]=[N:2]2)[CH:35]=[CH:34][C:29]=1[C:30]([O:32][CH3:33])=[O:31])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Komponenten

9

Edukt 4

HCID 1048PyrazoleHCID 8988D-Proline2×HCID 11430Potassium CarbonateHCID 66990993Methyl 2-(benzyloxy)-4-iodobenzoate

Produkt 1

HCID 66990761methyl 2-(benzyloxy)-4-(1H-pyrazol-1-yl)benzoateAusbeute 71,6 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Katalysator2×HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

1H-Pyrazole (0.044 g), D-proline (0.013 g), potassium carbonate (0.15 g), and copper(I) iodide (0.010 g) were added to a dimethyl sulfoxide (1.5 mL) solution of methyl 2-(benzyloxy)-4-iodobenzoate (0.20 g), followed by stirring under a nitrogen atmosphere at 90° C. for 2 hours. The reaction mixture was cooled to room temperature, and then D-proline (0.013 g) and copper(I) iodide (0.010 g) were added thereto, followed by stirring under a nitrogen atmosphere at 100° C. for 2 hours. After cooling the reaction mixture to room temperature, water and ethyl acetate were added thereto, and the insoluble substance was removed by filtration. The organic layer was separated, washed with water and a saturated aqueous solution of sodium chloride sequentially, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [Fuji Silysia Chemical Ltd., PSQ100B (spherical), eluent: 100-60% hexane/ethyl acetate] to obtain 0.12 g of methyl 2-(benzyloxy)-4-(1H-pyrazol-1-yl)benzoate as a white solid.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringby stirring under a nitrogen atmosphere at 100° C. for 2 hours
  3. temperatureAfter cooling the reaction mixture to room temperature
  4. customthe insoluble substance was removed by filtration
  5. customThe organic layer was separated
  6. washwashed with water
  7. dry with materiala saturated aqueous solution of sodium chloride sequentially, and dried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThe obtained residue was purified by silica gel column chromatography [Fuji Silysia Chemical Ltd., PSQ100B (spherical), eluent: 100-60% hexane/ethyl acetate]

Quellen und Nachweise

ORD-Eintrag
ord-a57a51c1170940d6bcb13bc84dc8a399
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492582B2

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