Triethylamine → 1-(6,7-dihydro-4H-furo[3,2-c]pyridin-5-yl)-6-phenylhexan-1-one

HRID 611090

Reaktionsgleichung

Reaktionsgleichung von HRID 611090
Cl.[O:2]1[C:10]2[CH2:9][CH2:8][NH:7][CH2:6][C:5]=2[CH:4]=[CH:3]1.[C:11]1([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22](O)=[O:23])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C.C(P(=O)(OCC)OCC)#N.[OH-].[Na+]>ClCCl>[O:2]1[C:10]2[CH2:9][CH2:8][N:7]([C:22](=[O:23])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:6][C:5]=2[CH:4]=[CH:3]1

Komponenten

7

Edukt 5

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 76257Diethyl cyanophosphonateHCID 796956-Phenylhexanoic AcidHCID 195999414,5,6,7-Tetrahydrofuro[3,2-c]pyridine hydrochloride

Produkt 1

HCID 196000411-(6,7-dihydro-4H-furo[3,2-c]pyridin-5-yl)-6-phenylhexan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 0.250 g (1.566 mmol) of 4,5,6,7-tetrahydrofuro[3,2-c]pyridine hydrochloride, 0.33 g (1.7 mmol) of 6-phenylhexanoic acid and 0.87 ml (6.3 mmol) of triethylamine in 30 ml of dichloromethane, 0.36 ml (2.4 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 chromatography (hexane/ethyl acetate=6/1 to 3/1) 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 chromatography (hexane/ethyl acetate=6/1 to 3/1)

Quellen und Nachweise

ORD-Eintrag
ord-6ec201416ced41c4bad2f6ecf37c45df
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US05998433

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