Sodium Carbonate → 5-(4-Tert-butylphenyl)furan-2-carbaldehyde

HRID 2197682

反応式

HRID 2197682 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:11])([CH3:10])[CH3:9])=[CH:4][CH:3]=1.[CH:12]([C:14]1[O:18][C:17](B(O)O)=[CH:16][CH:15]=1)=[O:13].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>[C:8]([C:5]1[CH:6]=[CH:7][C:2]([C:17]2[O:18][C:14]([CH:12]=[O:13])=[CH:15][CH:16]=2)=[CH:3][CH:4]=1)([CH3:11])([CH3:10])[CH3:9]

参加物

9

反応物 3

HCID 10340Sodium CarbonateHCID 775951-Bromo-4-tert-butylbenzeneHCID 27343555-Formylfuran-2-boronic acid

生成物 1

HCID 225667165-(4-Tert-butylphenyl)furan-2-carbaldehyde収率 995.6%

試薬・触媒・溶媒 5

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 962Water溶媒2 回HCID 80711,2-Dimethoxyethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a round bottom flask containing 1-bromo-4-tert-butyl-benzene (1.5 g, 7.04 mmol) and 5-formyl-2-furan-boronic acid (1.47 g, 10.56 mmol) in dimethoxyethane (80 mL) and ethanol (20 mL) was added an aqueous solution of sodium carbonate (2.24 g, 21.12 mmol) in water (30 mL) The reaction mixture was stirred at room temperature for 5 minutes, followed by the addition of tetrakis(triphenylphosphine)palladium (404 mg, 0.35 mmol). The reaction mixture was heated at 70° C. for 1 h. The reaction mixture was then cooled to room temperature and diluted with ethyl acetate (500 mL) and water (50 mL). The layers were separated and the aqueous layer was extracted with ethyl acetate (2×150 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 20% ethyl acetate in hexanes to afford 5-(4-tert-butyl-phenyl)-furan-2-carbaldehyde (1:16 g, 72%) as a dark brown solid. 1H NMR (400 MHz, CDCl3): δ 1.35 (9H, s), 6.80 (1H, d, J=3.6 Hz), 7.31 (1H, d, J=3.6 Hz), 7.44-7.7.48 (2H, m), 7.74-7.77 (2H, m), 9.64 (1H, s); APCI-MS: 228.34.

後処理

  1. temperatureThe reaction mixture was heated at 70° C. for 1 h
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with ethyl acetate (2×150 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 20% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-fb85345e7fc9469bb02a5a6a8eb88b7e
出典データセット
uspto-grants-2012_12
特許番号
US08338465B2

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