Dimethylformamide → 3-Benzofurancarboxylic acid, methyl ester

HRID 1091311

Reaktionsgleichung

Reaktionsgleichung von HRID 1091311
CN(C=[O:5])C.[O:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[C:8]([O:15]S(C(F)(F)F)(=O)=O)=[CH:7]1.C(N([CH2:28][CH3:29])CC)C>C1(P[C-]2C=CC=C2)C=CC=CC=1.[C-]1(PC2C=CC=CC=2)C=CC=C1.[Fe+2].C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CO>[CH3:7][O:6][C:10]([C:9]1[C:14]2[CH:13]=[CH:12][CH:11]=[CH:28][C:29]=2[O:15][CH:8]=1)=[O:5]

Komponenten

7

Edukt 3

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 21480510Benzo[b]furan-3-yl trifluoromethanesulfonate

Produkt 1

HCID 127770993-Benzofurancarboxylic acid, methyl esterAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 133083342Bis(cyclopenta-2,4-dien-1-yl(phenyl)phosphane);iron(2+)KatalysatorHCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a DMF (8.0 mL) solution of 1-benzofuran-3-yl trifluoromethanesulfonic acid (1.00 g, 3.76 mmol), 1,1′-diphenylphosphinoferrocene (128 mg, 231 μmol) and palladium acetate (26.0 mg, 116 μmol), methanol (3.5 mL) and triethylamine (1.05 mL, 7.53 mmol) were added thereto at room temperature. Carbon monoxide gas was bubbled for 20 minutes, and then under a carbon monoxide atmosphere, the mixture was heated and stirred at 60° C. for 3 hours. Water (50 mL) was added, and then the mixture was extracted with ethyl acetate (2×30 mL). The organic layer was combined, washed with 1N-hydrochloric acid (30 mL), and then dried over anhydrous magnesium sulfate. The solvent was concentrated under reduced pressure. The obtained residue was purified using silica gel flash column chromatography (Biotage AB: column No. 40M, hexane:diethyl ether=95:5), to obtain the title compound (570 mg, 3.24 mmol, 86%) as a transparent oily matter.

Aufarbeitung

  1. customat room temperature
  2. customCarbon monoxide gas was bubbled for 20 minutes
  3. temperatureunder a carbon monoxide atmosphere, the mixture was heated
  4. additionWater (50 mL) was added
  5. extractionthe mixture was extracted with ethyl acetate (2×30 mL)
  6. washwashed with 1N-hydrochloric acid (30 mL)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationThe solvent was concentrated under reduced pressure
  9. customThe obtained residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-4307a233a64144fb982e361feb07303a
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08129366B2

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