Potassium Carbonate → (Z)-methyl 3-(2-(3,4-difluorophenoxy)acetamido)but-2-enoate

HRID 56242

反応式

HRID 56242 の反応式
C([O-])([O-])=O.[K+].[K+].[F:7][C:8]1[CH:9]=[C:10]([OH:15])[CH:11]=[CH:12][C:13]=1[F:14].[CH3:16][O:17][C:18](=[O:27])/[CH:19]=[C:20](\[NH:22][C:23](=[O:26])[CH2:24]Br)/[CH3:21]>CC(C)=O>[F:7][C:8]1[CH:9]=[C:10]([CH:11]=[CH:12][C:13]=1[F:14])[O:15][CH2:24][C:23]([NH:22]/[C:20](/[CH3:21])=[CH:19]\[C:18]([O:17][CH3:16])=[O:27])=[O:26]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 759273,4-DifluorophenolHCID 90023822Methyl 3-(2-bromoacetamido)crotonate

生成物 1

HCID 90023321(Z)-methyl 3-(2-(3,4-difluorophenoxy)acetamido)but-2-enoate収率 59.6%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

To a suspension of K2CO3 (1.38 g, 10.0 mmol) in acetone (50 mL) were added 3,4-difluorophenol (0.78 g, 6.00 mmol) and (Z)-methyl-3-(2-bromoacetamido)but-2-enoate (1.18 g, 5.00 mmol) and the mixture was refluxed for 5 h. The mixture was cooled to rt and filtered and the filtrate was concentrated in vacuo. To the residue was added DCM (100 mL) and the mixture was washed with water (100 mL×2) and brine (100 mL), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=5:1) to give the title compound as a white solid (0.85 g, 59%).

後処理

  1. temperaturethe mixture was refluxed for 5 h
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated in vacuo
  4. additionTo the residue was added DCM (100 mL)
  5. washthe mixture was washed with water (100 mL×2) and brine (100 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by a silica gel column chromatography (PE/EtOAc (V/V)=5:1)

出典と根拠

ORDレコード
ord-ed3ce17cf6f94013ac2c4e9d743868d2
出典データセット
uspto-grants-2016_09
特許番号
US09434695B2

関連ノート

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