Iodoethane → Ethyl 3-bromofuran-2-carboxylate

HRID 1361899

反応式

HRID 1361899 の反応式
[Br:1][C:2]1[CH:6]=[CH:5][O:4][C:3]=1[C:7]([OH:9])=[O:8].[CH2:10](I)[CH3:11].C(=O)([O-])[O-].[Cs+].[Cs+].C(=O)([O-])O.[Na+]>C(#N)C>[Br:1][C:2]1[CH:6]=[CH:5][O:4][C:3]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

参加物

6

反応物 4

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 516892Sodium BicarbonateHCID 6054793-Bromofuran-2-carboxylic acid

生成物 1

HCID 22456149Ethyl 3-bromofuran-2-carboxylate収率 54.3%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

3-Bromofuran-2-carboxylic acid (1.86 g, 9.75 mmol), ethyl iodide (3.1 mL, 38.8 mol) and cesium carbonate (4.80 g, 14.7 mmol) were suspended in acetonitrile (50 mL), followed by stirring at 80° C. for 3 hours. Aqueous saturated sodium hydrogencarbonate solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=9:1) to afford ethyl 3-bromofuran-2-carboxylate (1.16 g, 54%).

後処理

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled away under reduced pressure
  4. customThe resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=9:1)

出典と根拠

ORDレコード
ord-d5bfc4c465ad4b3bbd3874a6474ffd1b
出典データセット
uspto-grants-2011_02
特許番号
US07880013B2

関連ノート

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