3-Methylcyclohexanol → HCID 22599683, Verbindung

HRID 1592284Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1592284
[H-].[Na+].[CH3:3][CH:4]1[CH2:9][CH2:8][CH2:7][CH:6]([OH:10])[CH2:5]1.[Cl:11][C:12]1[CH:17]=[C:16](Cl)[N:15]=[CH:14][N:13]=1.[Cl-].[NH4+]>O1CCCC1>[Cl:11][C:12]1[CH:17]=[C:16]([O:10][CH:6]2[CH2:7][CH2:8][CH2:9][CH:4]([CH3:3])[CH2:5]2)[N:15]=[CH:14][N:13]=1

Komponenten

6

Edukt 4

HCID 115663-MethylcyclohexanolHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 709434,6-Dichloropyrimidine

Produkt 1

HCID 22599683HCID 22599683, VerbindungAusbeute 50,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

In 5 ml of tetrahydrofuran was suspended 0.14 g of sodium hydride (60% in oil), to which 0.5 ml of a tetrahydrofuran solution containing 0.34 g of 3-methylcyclohexanol (mixture of cis-dorm and trans-form) was slowly added dropwise with stirring at room temperature. The mixture was stirred at room temperature for 10 minutes and then cooled to 0° C., to which 1.5 ml of a tetrahydrofuran solution containing 0.4 g of 4,6-dichloropyrimidine was slowly added dropwise, followed by further stirring at room temperature for 4 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution and extracted three times with t-butyl methyl ether. The organic layers were combined, washed with brine, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.31 g of 4-chloro-6-(3-methylcyclohexyloxy)pyrimidine.

Aufarbeitung

  1. additionwas slowly added dropwise
  2. stirringThe mixture was stirred at room temperature for 10 minutes
  3. additionwas slowly added dropwise
  4. stirringby further stirring at room temperature for 4 hours
  5. extractionextracted three times with t-butyl methyl ether
  6. washwashed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-9299bbeee0db42879c0b47e35b21344b
Quelldatensatz
uspto-grants-2007_11
Patentnummer
US07291730B2

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