Dimethyl (2-oxopropyl)phosphonate → 4-(Quinolin-3-yl)-but-3-en-2-one

HRID 1004283

Reaktionsgleichung

Reaktionsgleichung von HRID 1004283
[O:1]=[C:2]([CH3:10])[CH2:3]P(=O)(OC)OC.[Li+].[Cl-].[N:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[C:15]([CH:23]=O)[CH:14]=1.C1CCN2C(=NCCC2)CC1>C(#N)C>[N:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[C:15]([CH:23]=[CH:3][C:2](=[O:1])[CH3:10])[CH:14]=1

Komponenten

6

Edukt 4

HCID 77872Dimethyl (2-oxopropyl)phosphonateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 836413-QuinolinecarboxaldehydeHCID 433294Lithium Chloride

Produkt 1

HCID 541844574-(Quinolin-3-yl)-but-3-en-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

Dimethyl (2-oxopropyl)phosphonate (3.1 g,19.1 mmol), anhydrous LiCl (972 mg, 23 mmol), and 3-quinoline carboxaldehyde 6-1 (3.0 g,19.1 mmol) in anhydrous acetonitrile (70 mL), was treated with DBU (2.9 mL, 19.1 mmol) and the resulting suspension stirred at room temperature for 1 h. The solvent was removed at reduced pressure and the resulting residue partitioned between brine and methylene chloride. The organic layer was removed, dried, and concentrated to afford a yellow solid which was recrystallized from ethyl acetate/hexanes to afford 22-1 as an off-white solid.

Aufarbeitung

  1. customThe solvent was removed at reduced pressure
  2. customthe resulting residue partitioned between brine and methylene chloride
  3. customThe organic layer was removed
  4. customdried
  5. concentrationconcentrated
  6. customto afford a yellow solid which
  7. customwas recrystallized from ethyl acetate/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-2721a30731df47dbae90a5f4bb17a228
Quelldatensatz
uspto-grants-2000_04
Patentnummer
US06048861

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