Triethylamine → HCID 19600102, Verbindung

HRID 611300Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 611300
Cl.[O:2]1[C:6]2[CH2:7][NH:8][CH2:9][CH2:10][C:5]=2[CH:4]=[CH:3]1.[C:11]1([C:16]([C:18]2[CH:26]=[CH:25][C:21]([C:22](O)=[O:23])=[CH:20][CH:19]=2)=[O:17])[S:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C.C(P(=O)(OCC)OCC)#N.[OH-].[Na+]>ClCCl>[C:11]1([C:16]([C:18]2[CH:26]=[CH:25][C:21]([C:22]([N:8]3[CH2:9][CH2:10][C:5]4[CH:4]=[CH:3][O:2][C:6]=4[CH2:7]3)=[O:23])=[CH:20][CH:19]=2)=[O:17])[S:15][CH:14]=[CH:13][CH:12]=1

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 76257Diethyl cyanophosphonateHCID 195999074,5,6,7-Tetrahydrofuro[2,3-c]pyridine hydrochlorideHCID 196000994-(2-Thenoyl)benzoic acid

Produkt 1

HCID 19600102HCID 19600102, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 0.173 g (1.084 mmol) of 4,5,6,7-tetrahydrofuro[2,3-c]pyridine hydrochloride, 0.38 g (1.6 mmol) of 4-(2-thenoyl)benzoic acid and 0.60 ml (4.3 mmol) of triethylamine in 30 ml of dichloromethane, 0.25 ml (1.6 mmol) of diethyl cyanophosphonate was added dropwise at room temperature, followed by overnight stirring. This mixture was poured into aqueous sodium hydroxide and extracted with ethyl acetate 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 2/1) to yield the desired product.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-928a8a5151d94bd1a35ba129eeefdae8
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US05998433

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