Methanol → (S)-Cyclopent-1-enyl-hydroxyphenylacetic acid

HRID 1664701Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1664701
C([C@H]1[O:9][C:8](=[O:10])[C@:7]([C:17]2[CH2:21][CH2:20][CH2:19][CH:18]=2)([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:6]1)(C)(C)C.CO.O.[OH-].[K+]>[Cl-].[NH4+]>[C:17]1([C@:7]([OH:6])([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:8]([OH:10])=[O:9])[CH2:21][CH2:20][CH2:19][CH:18]=1

Komponenten

6

Edukt 4

HCID 887MethanolHCID 962WaterHCID 14797Potassium HydroxideHCID 67242157(2R,5S)-2-t-Butyl-5-cyclopent-1-enyl-5-phenyl-1,3-dioxolan-4-one

Produkt 1

HCID 67241271(S)-Cyclopent-1-enyl-hydroxyphenylacetic acidAusbeute 69,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 25517Ammonium ChlorideLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

Intermediate (1c) (540 mg, 1.9 mmol) was dissolved in MeOH (927 μL, 22.9 mmol). Water (1.84 mL, 102 mmol) was added, followed by the addition of KOH (1.1 g, 18.8 mmol). The reaction was refluxed at 130° C. for 3 hours. The mixture was diluted to 250 mL with saturated ammonium chloride, then washed (2×100 mL hexane). The remaining aqueous emulsion was washed (2×250 mL EtOAc). The EtOAc layers were combined, washed with 50 mL saturated aqueous NaCl, dried over Na2SO4, filtered and concentrated to yield intermediate (1d) as a brownish-yellow solid (290 mg).

Aufarbeitung

  1. washwashed (2×100 mL hexane)
  2. washThe remaining aqueous emulsion was washed (2×250 mL EtOAc)
  3. washwashed with 50 mL saturated aqueous NaCl
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-7299c97d23a048778f0a86270099e3f7
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08039489B2

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