tert-Butyl bromoacetate → HCID 58280086, Verbindung

HRID 2189034Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2189034
[C@H:1]1([OH:8])[CH2:6][CH2:5][CH2:4][C@H:3]([OH:7])[CH2:2]1.[C:9]([O:13][C:14](=[O:17])[CH2:15]Br)([CH3:12])([CH3:11])[CH3:10]>C1COCC1.ClCCl>[C:9]([O:13][C:14](=[O:17])[CH2:15][O:7][C@H:3]1[CH2:4][CH2:5][CH2:6][C@@H:1]([OH:8])[CH2:2]1)([CH3:12])([CH3:11])[CH3:10]

Komponenten

5

Edukt 2

HCID 79177tert-Butyl bromoacetateHCID 6432541HCID 6432541, Verbindung

Produkt 1

HCID 58280086HCID 58280086, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

Dissolve 5.0 g (43 mmol) of cis/trans-1,3-cyclohexanediol (approx. 1.2:1 cis/trans mixture) in 20 ml of absolute THF and, at RT, add 24.8 ml (approx. 49.5 mmol) of phosphazene base P2-t-Bu in THF (approx. 2 M solution) dropwise. Stir the solution at RT for a further 30 min and then add dropwise to a mixture of 9.5 ml (64.6 mmol) of bromoacetic acid tert-butyl ester and add 10 ml of THF dropwise. Stir the mixture at RT overnight, then dilute with dichloromethane, and wash the organic phase successively with 1N hydrochloric acid, buffer solution (pH 7) and sodium chloride solution, dry over sodium sulphate and concentrate under reduced pressure. Separate the crude product by means of chromatography on silica gel (eluent: cyclohexane/ethyl acetate 5:1→1:1). 2.73 g (27.6% of theory) of the cis-configured target compound are isolated as a pure fraction.

Aufarbeitung

  1. stirringStir the mixture at RT overnight
  2. washwash the organic phase successively with 1N hydrochloric acid, buffer solution (pH 7) and sodium chloride solution
  3. dry with materialdry over sodium sulphate
  4. concentrationconcentrate under reduced pressure
  5. customSeparate the crude product by means of chromatography on silica gel (eluent: cyclohexane/ethyl acetate 5:1→1:1)
  6. custom2.73 g (27.6% of theory) of the cis-configured target compound are isolated as a pure fraction

Quellen und Nachweise

ORD-Eintrag
ord-97a70ecfc51842bf89cc098d85df5eff
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08324222B2

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