m-Chloroperbenzoic acid → Methyl 2-(2-chloro-4-fluorophenyl)-3-(oxiran-2-yl)propanoate

HRID 451519Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 451519
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]([CH2:14][CH:15]=[CH2:16])[C:10]([O:12][CH3:13])=[O:11].ClC1C=CC=C(C(OO)=[O:25])C=1>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]([CH2:14][CH:15]1[CH2:16][O:25]1)[C:10]([O:12][CH3:13])=[O:11]

Komponenten

4

Edukt 2

HCID 70297m-Chloroperbenzoic acidHCID 67342147Methyl 2-(2-chloro-4-fluorophenyl)pent-4-enoate

Produkt 1

HCID 86656715Methyl 2-(2-chloro-4-fluorophenyl)-3-(oxiran-2-yl)propanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To an ice-cold solution of methyl 2-(2-chloro-4-fluorophenyl)pent-4-enoate (6.0 g, 24.7 mmol) in methylene chloride (50 mL) was added meta-chloroperbenzoic acid (6.7 g, 70% purity, 27.2 mmol). The cooling bath removed and the reaction stirred for 16 hours. The reaction was filtered, the filtrate washed repeatedly with 1 N sodium hydroxide, dried with sodium sulfate and the solvent was evaporated in vacuo. The residue was purified by column chromatography on silica gel using n-heptane/ethyl acetate (v/v 1:9 to 2:8) as eluent. The title compound was obtained as a colourless liquid (5.1 g, 80%).

Aufarbeitung

  1. customThe cooling bath removed
  2. filtrationThe reaction was filtered
  3. washthe filtrate washed repeatedly with 1 N sodium hydroxide
  4. dry with materialdried with sodium sulfate
  5. customthe solvent was evaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-876cf1e758fc4ed8bc107abda291739e
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08486967B2

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