Triethylamine → 6-(4-benzoylbenzoyl)-5,6,7,8-tetrahydro-4H-furo[2,3-d]azepine

HRID 611227Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 611227
Cl.[O:2]1[C:6]2[CH2:7][CH2:8][NH:9][CH2:10][CH2:11][C:5]=2[CH:4]=[CH:3]1.[C:12]([C:20]1[CH:28]=[CH:27][C:23]([C:24](O)=[O:25])=[CH:22][CH:21]=1)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C.C(P(=O)(OCC)OCC)#N.[OH-].[Na+]>ClCCl>[C:12]([C:20]1[CH:21]=[CH:22][C:23]([C:24]([N:9]2[CH2:10][CH2:11][C:5]3[CH:4]=[CH:3][O:2][C:6]=3[CH2:7][CH2:8]2)=[O:25])=[CH:27][CH:28]=1)(=[O:19])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 691474-Benzoylbenzoic acidHCID 76257Diethyl cyanophosphonateHCID 196002485,6,7,8-Tetrahydro-4H-furo[2,3-d]azepine Hydrochloride

Produkt 1

HCID 196001536-(4-benzoylbenzoyl)-5,6,7,8-tetrahydro-4H-furo[2,3-d]azepine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 0.128 g of the above crude 5,6,7,8-tetrahydro-4H-furo[2,3-d]azepine hydrochloride, 0.22 g (0.97 mmol) of 4-benzoylbenzoic acid and 0.45 ml (3.2 mmol) of triethylamine in 30 ml of dichloromethane, 0.15 ml (0.97 mmol) of diethyl cyanophosphonate was added dropwise under ice-cooling, followed by overnight stirring at room temperature. The reaction mixture was poured into aqueous sodium hydroxide and extracted with dichloromethane 3 times. The combined organic layer was dried over anhydrous magnesium 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 1/1) to yield the desired product.

Aufarbeitung

  1. temperaturecooling
  2. extractionextracted with dichloromethane 3 times
  3. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=3/1 to 1/1)

Quellen und Nachweise

ORD-Eintrag
ord-cbd87fcce67142c6aedcd24c54a1088d
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US05998433

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