Triethylamine → 6-(Anthraquinone-2-carbonyl)-4,5,6,7-tetrahydrofuro[2,3-c]pyridine

HRID 611137

Reaktionsgleichung

Reaktionsgleichung von HRID 611137
Cl.[O:2]1[C:6]2[CH2:7][NH:8][CH2:9][CH2:10][C:5]=2[CH:4]=[CH:3]1.[CH:11]1[C:24]2[C:23](=[O:25])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16](=[O:26])[C:15]=2[CH:14]=[CH:13][C:12]=1[C:27](O)=[O:28].C(N(CC)CC)C.C(P(=O)(OCC)OCC)#N>ClCCl.O>[CH:11]1[C:24]2[C:23](=[O:25])[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16](=[O:26])[C:15]=2[CH:14]=[CH:13][C:12]=1[C:27]([N:8]1[CH2:9][CH2:10][C:5]2[CH:4]=[CH:3][O:2][C:6]=2[CH2:7]1)=[O:28]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 670302-Anthraquinonecarboxylic acidHCID 76257Diethyl cyanophosphonateHCID 195999074,5,6,7-Tetrahydrofuro[2,3-c]pyridine hydrochloride

Produkt 1

HCID 195999636-(Anthraquinone-2-carbonyl)-4,5,6,7-tetrahydrofuro[2,3-c]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 0.160 g (1.000 mmol) of 4,5,6,7-tetrahydrofuro[2,3-c]pyridine hydrochloride, 0.302 g (1.2 mmol) of anthraquinone-2-carboxylic acid and 0.55 ml (4.0 mmol) of triethylamine in 30 ml of dichloromethane, 0.24 g (1.5 mmol) of diethyl cyanophosphonate was added under ice-cooling, followed by overnight stirring at room temperature. The reaction mixture was poured into water and extracted with dichloromethane 2 times. The combined organic layer was washed with water and dried over anhydrous sodium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=3/1 to 2/1); the resulting solid was washed with ethyl acetate to yield the desired product.

Aufarbeitung

  1. temperaturecooling
  2. extractionextracted with dichloromethane 2 times
  3. washThe combined organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=3/1 to 2/1)
  7. washthe resulting solid was washed with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-200035bc39454bcb9d92fd4df9cd3b4a
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US05998433

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