Diisopropylamine → 1-(2-Chlorophenyl)-2-(pyridin-4-yl)ethanone

HRID 1167651Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1167651
C(NC(C)C)(C)C.C([Li])CCC.[N:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1.CC1N([C:24]([C:26]2[C:31]([Cl:32])=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:25])C1>O1CCCC1.CCCCCC.O>[Cl:32][C:31]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1[C:24](=[O:25])[CH2:19][C:16]1[CH:17]=[CH:18][N:13]=[CH:14][CH:15]=1

Komponenten

8

Edukt 4

HCID 7912DiisopropylamineHCID 79634-MethylpyridineHCID 592159Aziridine, 1-(o-chlorobenzoyl)-2-methyl-HCID 178418339Butyllithium

Produkt 1

HCID 113792481-(2-Chlorophenyl)-2-(pyridin-4-yl)ethanoneAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel3×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

To a stirred solution of diisopropylamine (15.4 mL) in dry tetrahydrofuran (100 mL) cooled at −50° C., was added a solution of 1.6 M n-butyllithium in hexane (69 mL) dropwise. After addition, the resulting mixture was stirred for 10 min at the same temperature, followed by the addition of a solution of γ-picoline (20 g) in dry tetrahydrofuran (10 mL) at −30° C. After an additional 1 h stirring, a solution of N-(2-chlorobenzoyl)propyleneimine (20 g) in dry tetrahydrofuran (10 mL) was added dropwise to the resulting mixture at −10° C. After addition the mixture was stirred for another 2 h at ambient temperature. Water (100 mL) was added to the mixture and extracted with ethyl acetate. The extract was washed with water, dried, and concentrated under reduced pressure. The residue was purified using silica-gel column chromatography (hexane-ethyl acetate, 1:1) to give the title compound (16.4 g, yield 71%).

Aufarbeitung

  1. additionAfter addition
  2. stirringAfter an additional 1 h stirring
  3. additionAfter addition the mixture
  4. stirringwas stirred for another 2 h at ambient temperature
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with water
  7. customdried
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-794df2412a9a4181a391a639ba30819b
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06620825B1

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