Water → 2'-Fluoro-5'-methoxy-2-(1-methoxy-2,2-dimethyl-but-3-enyl)-biphenyl-4-carboxylic acid methyl ester

HRID 2098943ノート

反応式

HRID 2098943 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:12]=2[F:19])=[C:7]([CH:20]([OH:26])[C:21]([CH3:25])([CH3:24])[CH:22]=[CH2:23])[CH:6]=1)=[O:4].[H-].[Na+].[CH3:29]I.O>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:12]=2[F:19])=[C:7]([CH:20]([O:26][CH3:29])[C:21]([CH3:25])([CH3:24])[CH:22]=[CH2:23])[CH:6]=1)=[O:4]

参加物

6

反応物 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 574676322'-Fluoro-2-(1-hydroxy-2,2-dimethyl-but-3-enyl)-5'-methoxy-biphenyl-4-carboxylic acid methyl ester

生成物 1

HCID 577061812'-Fluoro-5'-methoxy-2-(1-methoxy-2,2-dimethyl-but-3-enyl)-biphenyl-4-carboxylic acid methyl ester収率 47.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of T21.4 (1530 mg, 4269 μmol) in DMF (40 mL), was added sodium hydride (60% in oil) (213 μL, 8538 μmol). The mixture was stirred at room temperature for 10 minutes and then methyl iodide (530 μL, 8538 μmol) was added in one portion and the mixture was stirred at room temperature for 30 minutes. Water was added and the mixture was, extracted with EtOAc. The organic phase was washed with water and brine and then dried over anhydrous sodium sulfate. After filtration, the organic solvent was removed in vacuo to give the product as a residue which was purified by chromatography to give the product as an oil (0.75 g, 47%). MS ESI m/e: 373.2 (M+18)+.

後処理

  1. stirringthe mixture was stirred at room temperature for 30 minutes
  2. extractionextracted with EtOAc
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. customthe organic solvent was removed in vacuo
  7. customto give the product as a residue which
  8. customwas purified by chromatography

出典と根拠

ORDレコード
ord-194bab8db3604498a3c53ffab3e9e3d4
出典データセット
uspto-grants-2013_05
特許番号
US08450522B2

反応ノート

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