Methanol → (R)-Methyl 2-(3-chlorophenyl)-2-hydroxyacetate

HRID 547099Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 547099
C[Si](C=[N+]=[N-])(C)C.[CH3:8]CCCCC.[Cl:14][C:15]1[CH:16]=[C:17]([C@@H:21]([OH:25])[C:22]([OH:24])=[O:23])[CH:18]=[CH:19][CH:20]=1.CO>C1C=CC=CC=1>[CH3:8][O:23][C:22](=[O:24])[C@@H:21]([C:17]1[CH:18]=[CH:19][CH:20]=[C:15]([Cl:14])[CH:16]=1)[OH:25]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 8058HexaneHCID 167693TrimethylsilyldiazomethaneHCID 2733127(R)-2-(3-Chlorophenyl)-2-hydroxyacetic acid

Produkt 1

HCID 15606324(R)-Methyl 2-(3-chlorophenyl)-2-hydroxyacetateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

A solution of trimethylsilyldiazomethane in hexane (2 M, 1.5 mL, 3.0 mmol) was added to a solution of (R)-(3-chloro-phenyl)hydroxy-acetic acid (497 mg, 2.66 mmol) in benzene (2.6 mL)-methanol (1.3 mL) under cooling with ice. Then, the ice bath was removed and the mixture was stirred at room temperature for five minutes. The reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate=3/1) to give the title compound (533 mg, 100%).

Aufarbeitung

  1. temperatureunder cooling with ice
  2. customThen, the ice bath was removed
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate=3/1)

Quellen und Nachweise

ORD-Eintrag
ord-acb4e590f4b54af78e766fdbdfa59cb8
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07935688B2

Notizen zur Reaktion

Wird geladen…