Diisopropylamine → 4-[2-Hydroxy-1,1-dimethyl-3-(4-pyrimidinyl)-2-propenyloxy]benzonitrile

HRID 1073952

Reaktionsgleichung

Reaktionsgleichung von HRID 1073952
C([Li])CCC.C(NC(C)C)(C)C.[CH3:13][C:14]1[CH:19]=[CH:18][N:17]=[CH:16][N:15]=1.[C:20]([C:22]1[CH:36]=[CH:35][C:25]([O:26][C:27]([CH3:34])([CH3:33])[C:28](OCC)=[O:29])=[CH:24][CH:23]=1)#[N:21]>CCCCCC.O1CCCC1>[OH:29][C:28](=[CH:13][C:14]1[CH:19]=[CH:18][N:17]=[CH:16][N:15]=1)[C:27]([CH3:34])([CH3:33])[O:26][C:25]1[CH:35]=[CH:36][C:22]([C:20]#[N:21])=[CH:23][CH:24]=1

Komponenten

7

Edukt 4

HCID 7912DiisopropylamineHCID 189224-MethylpyrimidineHCID 205808Propanoic acid, 2-(4-cyanophenoxy)-2-methyl-, ethyl esterHCID 178418339Butyllithium

Produkt 1

HCID 1364045254-[2-Hydroxy-1,1-dimethyl-3-(4-pyrimidinyl)-2-propenyloxy]benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel3×HCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

10 ml of a 1.2M solution of butyllithium in n-hexane were added to a solution of 1.68 ml of diisopropylamine in 50 ml of tetrahydrofuran while stirring at -78° C. under a nitrogen atmosphere. The solution was stirred for a further 15 minutes and a solution of 4-methylpyrimidine in 20 ml of tetrahydrofuran was then added. The solution was allowed to warm to 20° C. and was stirred for 2 hours. The solution was then cooled to -78° C., 2.33 g of ethyl 2-(4-cyanophenoxy)-2-methylpropionate in 30 ml of tetrahydrofuran were added to and the mixture was allowed to warm to 20° C. and was stirred for 16 hours. The mixture was then partitioned between ethyl acetate and water. The organic phase was washed with sodium chloride solution and evaporated. The residue was chromatographed on silica gel using ethyl acetate for the elution to give 0.69 g of 4-[2-hydroxy-1,1-dimethyl-3-(4-pyrimidinyl)-2-propenyloxy]benzonitrile in the form of a yellow solid of melting point 115°-117° C. (from ethyl acetate/n-hexane).

Aufarbeitung

  1. stirringThe solution was stirred for a further 15 minutes
  2. temperatureto warm to 20° C.
  3. stirringwas stirred for 2 hours
  4. temperatureThe solution was then cooled to -78° C.
  5. temperatureto warm to 20° C.
  6. stirringwas stirred for 16 hours
  7. customThe mixture was then partitioned between ethyl acetate and water
  8. washThe organic phase was washed with sodium chloride solution
  9. customevaporated
  10. customThe residue was chromatographed on silica gel
  11. washfor the elution

Quellen und Nachweise

ORD-Eintrag
ord-6b5200dcbc2f40e8a9cdfe38177c1cc0
Quelldatensatz
uspto-grants-1990_11
Patentnummer
US04971982

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