Ethanol → Methyl 2-[(5-benzofuranyloxy)methyl]benzoate

HRID 1070470ノート

反応式

HRID 1070470 の反応式
Br[CH2:2][C:3]1[C:4]([C:9]([O:11][CH3:12])=[O:10])=[CH:5][CH:6]=[CH:7][CH:8]=1.[C:13](=[O:16])([O-])[O-].[K+].[K+].[CH2:19]([OH:21])[CH3:20]>C(OCC)(=O)C.O.[C].[Pd]>[O:21]1[C:3]2[CH:4]=[CH:5][C:13]([O:16][CH2:2][C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=3[C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:8]=2[CH:20]=[CH:19]1.[O:21]1[C:3]2[CH:4]=[CH:5][C:13]([O:16][CH2:2][C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=3[C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:8]=2[CH2:20][CH2:19]1

参加物

8

反応物 3

HCID 702EthanolHCID 11430Potassium CarbonateHCID 2734813Methyl 2-(bromomethyl)benzoate

生成物 2

HCID 22397060HCID 22397060、化合物収率 17%HCID 22397069Methyl 2-[(5-benzofuranyloxy)methyl]benzoate収率 27%

試薬・触媒・溶媒 3

HCID 178418390HCID 178418390、化合物触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒2 回

反応条件

温度
100 °C

実験手順

5-(Benzyloxy)benzofuran (1.02 g, 4.55 mmol) obtained in Preparation Example 2-4, Step 2 was dissolved in a mixed solvent of ethanol (5 ml) and ethyl acetate (5 ml) and 5% palladium carbon (500 mg) was added, which was followed by hydrogenation at room temperature under normal pressure. After 2 hr, the reaction mixture was passed through celite and the filtrate was concentrated under reduced pressure. The residue was dissolved in dimethylformamide (20 ml) and methyl α-bromo-o-toluate (1.042 g, 4.55 mmol) and potassium carbonate (1.26 g, 9.10 mmol) were added. The mixture was heated at 100° C. for 1.25 hr and cooled to room temperature. The reaction mixture was diluted with water and ethyl acetate to separate the layers. The organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to give methyl 2-[(5-benzofuranyloxy)methyl]benzoate (352 mg, 27%, white crystals) and methyl 2-[(2,3-dihydrobenzofuran-5-yloxy)methyl]benzoate (220 mg, 17%, pale-yellow oil).

後処理

  1. additionwas added
  2. customwas followed by hydrogenation at room temperature under normal pressure
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. dissolutionThe residue was dissolved in dimethylformamide (20 ml)
  5. temperaturecooled to room temperature
  6. customto separate the layers
  7. washThe organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and saturated brine
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)

出典と根拠

ORDレコード
ord-103b8f5582974fff85c8a333a754cb11
出典データセット
uspto-grants-2005_06
特許番号
US06903094B2

反応ノート

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