Methyl acetoacetate → HCID 131719005, Verbindung

HRID 36919

Reaktionsgleichung

Reaktionsgleichung von HRID 36919
[C:1]([O:7][CH3:8])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[H-].[Na+].[CH2:11]([Li])CCC.[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[C:28](/[CH:29]=[CH:30]/[CH:31]=[O:32])=[C:27]([CH:33]([CH3:35])[CH3:34])[N:26]=[C:25]([O:36][CH3:37])[C:24]=2COC)=[CH:19][CH:18]=1.[O:41]1CCC[CH2:42]1>CCCCCC.CCOCC.[Cl-].[NH4+].[Cl-].[Zn+2].[Cl-]>[F:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]2[C:28](/[CH:29]=[CH:30]/[CH:31]([OH:32])[CH2:5][C:3](=[O:4])[CH2:2][C:1]([O:7][CH3:8])=[O:6])=[C:27]([CH:33]([CH3:35])[CH3:34])[N:26]([CH3:11])[CH:25]([O:36][CH3:37])[C:24]=2[O:41][CH3:42])=[CH:21][CH:22]=1

Komponenten

10

Edukt 5

HCID 7757Methyl acetoacetateHCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 19936689(E)-3-[4-(4-Fluorophenyl)-6-isopropyl-2-methoxy-3-methoxymethyl-pyridin-5-yl]-prop-2-enalHCID 178418339Butyllithium

Produkt 1

HCID 131719005HCID 131719005, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 3007855ZincchlorideKatalysatorHCID 3283Diethyl EtherLösungsmittelHCID 8058HexaneLösungsmittelHCID 25517Ammonium ChlorideLösungsmittel

Versuchsvorschrift

0.35 ml (3.3 mmol) of methyl acetoacetate are added dropwise under nitrogen to a suspension of 80 mg (3.4 mmol) of sodium hydride in 3 ml of dry tetrahydrofuran at -5° C. After 15 min, 2.3 ml (3.3 mmol) of 15% strength butyllithium in n-hexane and 3.3 ml (3.3 mmol) of a 1 molar zinc chloride solution in ether are added dropwise at the same temperature and the mixture is stirred for 15 min. 530 mg (1.5 mmol) of the compound from Example 10 dissolved in 8 ml of dry tetrahydrofuran are then added dropwise and the mixture is stirred at -5° C. for 30 min. The reaction solution is cautiously diluted with 100 ml of saturated aqueous ammonium chloride solution and the mixture is extracted three times with 100 ml of ether each time. The combined organic phases are washed twice with saturated sodium hydrogen carbonate solution and once with saturated sodium chloride solution, dried over sodium sulphate and concentrated in vacuo.

Aufarbeitung

  1. additionare then added dropwise
  2. stirringthe mixture is stirred at -5° C. for 30 min
  3. extractionthe mixture is extracted three times with 100 ml of ether each time
  4. washThe combined organic phases are washed twice with saturated sodium hydrogen carbonate solution and once with saturated sodium chloride solution
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b62755906215485e999eb3fe515012ae
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05418243

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