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

HRID 611270
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 611270
Cl.[O:2]1[C:6]2[CH2:7][NH:8][CH2:9][CH2:10][C:5]=2[CH:4]=[CH:3]1.[CH3:11][C:12]1[CH:28]=[CH:27][CH:26]=[CH:25][C:13]=1[C:14]([C:16]1[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[CH:18][CH:17]=1)=[O:15].C(N(CC)CC)C.C(P(=O)(OCC)OCC)#N>ClCCl.O>[CH3:11][C:12]1[CH:28]=[CH:27][CH:26]=[CH:25][C:13]=1[C:14]([C:16]1[CH:24]=[CH:23][C:19]([C:20]([N:8]2[CH2:9][CH2:10][C:5]3[CH:4]=[CH:3][O:2][C:6]=3[CH2:7]2)=[O:21])=[CH:18][CH:17]=1)=[O:15]
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Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 180011004-(2-Methylbenzoyl)benzoic acidHCID 195999074,5,6,7-Tetrahydrofuro[2,3-c]pyridine hydrochloride

Produkt 1

HCID 196000596-[4-(2-Methylbenzoyl)benzoyl]-4,5,6,7-tetrahydrofuro[2,3-c]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 0.160 g (1.000 mmol) of 4,5,6,7-tetrahydrofuro[2,3-c]pyridine hydrochloride, 0.288 g (1.2 mmol) of 4-(2-methylbenzoyl)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=3/1) 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)

Quellen und Nachweise

ORD-Eintrag
ord-4619257ad63d4cb8a2972bab7162ca9c
Quelldatensatz
uspto-grants-1999_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05998433

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