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

HRID 2187600노트

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HRID 2187600 반응식
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

참가 물질

8

반응물 3

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

생성물 2

HCID 22397060HCID 22397060, 화합물수율 17%HCID 22397069Methyl 2-[(5-benzofuranyloxy)methyl]benzoate수율 27%

시약·촉매·용매 3

HCID 178418390HCID 178418390, 화합물촉매HCID 962Water용매HCID 8857Ethyl Acetate용매2회

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온도
100 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-cdc4ab544a4f4b8a956ed67fb7000bc3
출처 데이터셋
uspto-grants-2002_06
특허 번호
US06410561B1

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