Water → 3-(4-Cyano-2-fluoro-phenyl)-5-methoxy-4,5-dihydro-isoxazole-5-carboxylic acid methyl ester

HRID 1424530Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1424530
[CH2:1](N(CC)CC)C.Cl[O:9][N:10]=[CH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[CH:14][C:13]=1[F:20].[CH3:21][O:22][C:23](=[CH2:27])[C:24]([O-:26])=[O:25].O>ClCCl>[CH3:1][O:25][C:24]([C:23]1([O:22][CH3:21])[O:9][N:10]=[C:11]([C:12]2[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[CH:14][C:13]=2[F:20])[CH2:27]1)=[O:26]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 219344252-MethoxyacrylateHCID 866861574-Cyano-2-fluoro-benzaldehyde chlorooxime

Produkt 1

HCID 866861563-(4-Cyano-2-fluoro-phenyl)-5-methoxy-4,5-dihydro-isoxazole-5-carboxylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Triethylamine (1.05 mL) is added drop wise to a mixture of (4-cyano-2-fluoro-benzaldehyde chlorooxime (600 mg) and 2-methoxyacrylate (421 mg) in dichloromethane (7.5 mL). The reaction mixture is stirred over night at room temperature. Water is added and the aqueous phase is extracted with ethyl acetate. The combined organic phases are washed with brine, dried over MgSO4, and concentrated in vacuo. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 80:20→50:50) to afford the title compound. LC (method 4): tR=0.93 min; Mass spectrum (ESI+): m/z=279 [M+H]+.

Aufarbeitung

  1. extractionthe aqueous phase is extracted with ethyl acetate
  2. washThe combined organic phases are washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 80:20→50:50)

Quellen und Nachweise

ORD-Eintrag
ord-68d70afe4f6248ffa47e6f89e88110ee
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08927726B2

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