Magnesium perchlorate → HCID 178472492, Verbindung

HRID 237328

Reaktionsgleichung

Reaktionsgleichung von HRID 237328
[CH2:1]([O:3][C:4]([C@H:6]1[CH2:11][CH2:10][C@H:9]([OH:12])[CH2:8][CH2:7]1)=[O:5])[CH3:2].Cl([O-])(=O)(=O)=O.[Mg+2].Cl([O-])(=O)(=O)=O>ClCCl>[CH2:1]([O:3][C:4]([C@H:6]1[CH2:11][CH2:10][C@H:9]([O:12][C:6]([CH3:11])([CH3:7])[CH3:4])[CH2:8][CH2:7]1)=[O:5])[CH3:2].[CH2:1]([O:3][C:4]([C@H:6]1[CH2:11][CH2:10][C@@H:9]([O:12][C:6]([CH3:11])([CH3:7])[CH3:4])[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Komponenten

5

Edukt 2

HCID 24840Magnesium perchlorateHCID 178472487HCID 178472487, Verbindung

Produkt 2

HCID 178472492HCID 178472492, VerbindungHCID 178472493HCID 178472493, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a solution of cis/trans-4-hydroxycyclohexane carboxylic acid ethyl ester (2:1) (1.0 g, 5.8 mmol) and di-tort-butyl dicarbonate (2.9 g, 13.4 mmol) in dichloromethane (6 ml) was added anhydrous magnesium perchlorate (0.13 g, 0.58 mmol) which was previously activated in high vacuo (ca. 1 mbar) at 150° C. for 1 h. Stirring for 16 h at 40° C. was followed by partitioning between dichloromethane (50 ml) and water (30 ml). The layers were separated. The aqueous layer was extracted with one 50-ml portion of dichloromethane. The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo. Purification by flash-chromatography with n-heptane/tert-butyl methyl ether as eluent gave pure trans-4-tert-butoxy-cyclohexanecarboxylic acid ethyl ester and cis-4-tert-butoxy-cyclohexanecarboxylic acid ethyl ester.

Aufarbeitung

  1. customby partitioning between dichloromethane (50 ml) and water (30 ml)
  2. customThe layers were separated
  3. extractionThe aqueous layer was extracted with one 50-ml portion of dichloromethane
  4. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customPurification by flash-chromatography with n-heptane/tert-butyl methyl ether as eluent

Quellen und Nachweise

ORD-Eintrag
ord-ff3942f6ef564a28963eefe7a0353ea6
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642590B2

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