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

HRID 1424530Notes

Reaction equation

HRID 1424530 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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]+.

Workup

  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)

Sources & evidence

ORD record
ord-68d70afe4f6248ffa47e6f89e88110ee
Source dataset
uspto-grants-2015_01
Patent number
US08927726B2

Reaction notes

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