Citric Acid → HCID 178472501, Verbindung

HRID 2059987Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2059987
Cl[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3].[OH:9][CH:10]1[CH2:15][CH2:14][CH:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:12][CH2:11]1.N1C=CN=C1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C)C=O>[CH3:6][C:5]([Si:2]([CH3:4])([CH3:3])[O:9][C@H:10]1[CH2:11][CH2:12][C@H:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:14][CH2:15]1)([CH3:8])[CH3:7]

Komponenten

6

Edukt 4

HCID 311Citric AcidHCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 86973Ethyl 4-hydroxycyclohexanecarboxylate

Produkt 1

HCID 178472501HCID 178472501, VerbindungAusbeute 101,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

Chloro(1,1-dimethylethyl)dimethylsilane (115 g; 0.76 mol) was added in portions over 1 hour to a solution of commercially available ethyl 4-hydroxycyclohexanecarboxylate (118 g; 0.68 mol), imidazole (103 g; 1.52 mol) and dimethylformamide (400 mL) stirred under an atmosphere of argon. A small exotherm was observed resulting in the reaction mixture temperature increasing to ˜40° C. The mixture was stirred at room temperature overnight then poured into 10% citric acid solution (2 L) and extracted with diethyl ether (2×800 mL). The ether extracts were washed with water, brine and then dried (Na2SO4) and the solvent was removed to give the title compound as an oil (198.4 g)

Aufarbeitung

  1. customA small exotherm was observed resulting in the reaction mixture temperature
  2. stirringThe mixture was stirred at room temperature overnight
  3. extractionextracted with diethyl ether (2×800 mL)
  4. washThe ether extracts were washed with water, brine
  5. dry with materialdried (Na2SO4)
  6. customthe solvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-10e53d6dc7ec48f3987e77022584ce24
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08278328B2

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