Triethylamine → HCID 19600137, Verbindung

HRID 611163Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 611163
Cl.[O:2]1[C:10]2[CH2:9][CH2:8][NH:7][CH2:6][C:5]=2[CH:4]=[CH:3]1.[Cl:11][C:12]1[CH:28]=[CH:27][C:15]([C:16]([C:18]2[CH:26]=[CH:25][C:21]([C:22](O)=[O:23])=[CH:20][CH:19]=2)=[O:17])=[CH:14][CH:13]=1.C(N(CC)CC)C.C(P(=O)(OCC)OCC)#N>ClCCl.O>[Cl:11][C:12]1[CH:28]=[CH:27][C:15]([C:16]([C:18]2[CH:26]=[CH:25][C:21]([C:22]([N:7]3[CH2:8][CH2:9][C:10]4[O:2][CH:3]=[CH:4][C:5]=4[CH2:6]3)=[O:23])=[CH:20][CH:19]=2)=[O:17])=[CH:14][CH:13]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 2338394-(4-Chlorobenzoyl)benzoic acidHCID 195999414,5,6,7-Tetrahydrofuro[3,2-c]pyridine hydrochloride

Produkt 1

HCID 19600137HCID 19600137, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 0.160 g (1.000 mmol) of 4,5,6,7-tetrahydrofuro[3,2-c]pyridine hydrochloride, 0.287 g (1.1 mmol) of 4-(4-chlorobenzoyl)benzoic 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 dropwise 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/dichloromethane=4/1/1), after which it was recrystallized from hexane-methanol 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/dichloromethane=4/1/1)
  7. customafter which it was recrystallized from hexane-methanol

Quellen und Nachweise

ORD-Eintrag
ord-5ca74f8a5e824c74b9892306cdead56c
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US05998433

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