Sodium Carbonate → Methyl 5-(pyridin-4-yl)furan-2-carboxylate

HRID 278556

Reaktionsgleichung

Reaktionsgleichung von HRID 278556
Br[C:2]1[O:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[CH:4][CH:3]=1.[N:11]1[CH:16]=[CH:15][C:14](OB(O)O)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.C(OCC)(=O)C>[N:11]1[CH:16]=[CH:15][C:14]([C:2]2[O:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[CH:4][CH:3]=2)=[CH:13][CH:12]=1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 599633Methyl 5-bromofuran-2-carboxylateHCID 218058124-Pyridylboric acid

Produkt 1

HCID 22627954Methyl 5-(pyridin-4-yl)furan-2-carboxylateAusbeute 17,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 80711,2-DimethoxyethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of methyl 5-bromo-2-furancarboxylate (820 mg), 4-pyridyl boric acid (500 mg), tetrakistriphenyl-phosphine palladium(0) (250 mg) in dimethoxyethane (15 ml) was added 2 M sodium carbonate solution (4 ml) and the solution was heated for 15 hours under reflux. The reaction solution was diluted with ethyl acetate, and the organic layer was separated, washed with water, extracted with 1 N hydrochloric acid. The extract was made alkaline with sodium hydroxide solution, extracted with ethyl acetate, dried and concentrated to give a colorless solid of methyl 5-(4-pyridyl)-2-furancarboxylate (126 mg). 1H-NMR (CDCl3) δ: 3.94 (3H, s), 6.96 (1H, d, J=3.8 Hz), 7.27 (1H, d, J=3.8 Hz), 7.64 (2H, d, J=6.2 Hz), 8.68 (2H, d, J=6.2 Hz). IR (KBr): 1727, 1608, 13.7, 1145 cm−1.

Aufarbeitung

  1. temperaturethe solution was heated for 15 hours
  2. temperatureunder reflux
  3. customthe organic layer was separated
  4. washwashed with water
  5. extractionextracted with 1 N hydrochloric acid
  6. extractionextracted with ethyl acetate
  7. customdried
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-0ad3fded4eb44ab9994f87ef46f42992
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06359134B1

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