Sodium Carbonate → 5-(4-Benzyl-phenyl)-furan-2-carbaldehyde

HRID 2197674

반응식

HRID 2197674 반응식
[CH2:1]([C:8]1[CH:13]=[CH:12][C:11](Br)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:15]([C:17]1[O:21][C:20](B(O)O)=[CH:19][CH:18]=1)=[O:16].C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.C(O)C.O.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([C:8]1[CH:13]=[CH:12][C:11]([C:20]2[O:21][C:17]([CH:15]=[O:16])=[CH:18][CH:19]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

9

반응물 3

HCID 10340Sodium CarbonateHCID 2360001-Benzyl-4-bromobenzeneHCID 27343555-Formylfuran-2-boronic acid

생성물 1

HCID 594462325-(4-Benzyl-phenyl)-furan-2-carbaldehyde수율 43.1%

시약·촉매·용매 5

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 962Water용매2회HCID 80711,2-Dimethoxyethane용매HCID 8857Ethyl Acetate용매

실험 절차

To a round bottom flask containing 1-benzyl-4-bromo-benzene (700 mg, 2.83 mmol) and 5-formyl-2-furan-boronic acid (595 mg, 4.25 mmol) in dimethoxyethane (30 mL) and ethanol (7.5 mL) was added an aqueous solution of sodium carbonate (900 mg, 8.49 mmol) in water (10 mL) The reaction mixture was stirred at room temperature for 5 minutes, followed by the addition of tetrakis(triphenylphosphine)palladium (162 mg, 0.14 mmol). The reaction was heated at 70° C. for 1 h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (200 mL) and water (20 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (2×50 mL). The combined organic extracts were washed with brine, dried (sodium sulfate) and concentrated under vacuum. The crude product was purified by silica gel chromatography eluting with 6% ethyl acetate in hexanes to afford 5-(4-benzyl-phenyl)-furan-2-carbaldehyde (320 mg g, 43%) as a solid. 1H NMR (400 MHz, DMSO-d6) δ 3.99 (2H, s), 7.20-7.39 (8H, m), 7.63 (1H, d, J=3.6 Hz), 7.78-7.81 (2H, m), 9.59 (1H, s); APCI-MS: 262.02.

후처리

  1. temperatureThe reaction was heated at 70° C. for 1 h
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with ethyl acetate (2×50 mL)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (sodium sulfate)
  7. concentrationconcentrated under vacuum
  8. customThe crude product was purified by silica gel chromatography
  9. washeluting with 6% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-126ebf6910424dcaaaaa3d9c6536efe0
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08338465B2

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