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

HRID 1424530ノート

反応式

HRID 1424530 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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]+.

後処理

  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)

出典と根拠

ORDレコード
ord-68d70afe4f6248ffa47e6f89e88110ee
出典データセット
uspto-grants-2015_01
特許番号
US08927726B2

反応ノート

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