Methyl iodide → HCID 274359, Verbindung

HRID 1247699Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1247699
Br[C:2]1([Br:17])[CH2:4][C:3]1([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH2:18]([Li])CCC.CCCCCC.CI>O.C1COCC1>[Br:17][C:2]1([CH3:18])[CH2:4][C:3]1([C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Komponenten

7

Edukt 4

HCID 6328Methyl iodideHCID 8058HexaneHCID 2912041,1-Dibromo-2,2-diphenylcyclopropaneHCID 178418339Butyllithium

Produkt 1

HCID 274359HCID 274359, VerbindungAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-70 °C

Versuchsvorschrift

Under a nitrogen atmosphere, 1,1-dibromo-2,2-diphenylcyclopropane(10.6 g, 30.0 mmol) obtained in Example 1-(1) and THF (tetrahydrofuran, 120 ml) were placed in a reaction flask and cooled to −70° C. To the mixture, n-butyllithium in hexane (20 ml, 1.57M, 31.4 mmol) was added gradually, and the mixture was stirred at the same temperature for 30 minutes. Methyl iodide (2.1 ml, 33 mmol) was added to the reaction mixture and the resulting mixture was stirred for 30 minutes and then warmed to room temperature. Then, water was added to the reaction mixture and the organic layer was extracted with toluene. The toluene extract was dried over anhydrous magnesium sulfate and then the solvent was removed under reduced pressure. The residue was recrystallized from methanol to give the title compound (7.28 g, 89%) as white crystal.

Aufarbeitung

  1. stirringthe resulting mixture was stirred for 30 minutes
  2. temperaturewarmed to room temperature
  3. extractionthe organic layer was extracted with toluene
  4. extractionThe toluene extract
  5. dry with materialwas dried over anhydrous magnesium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was recrystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-925d27d2d84d48f3850e1408e563b9ed
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07129367B2

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