Potassium Carbonate → 2-(4-Nitrophenyl)oxirane

HRID 387228

Reaktionsgleichung

Reaktionsgleichung von HRID 387228
[N+:1]([C:4]1[CH:13]=[CH:12][C:7]([C:8](=[O:11])[CH2:9]Br)=[CH:6][CH:5]=1)([O-:3])=[O:2].[BH4-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CO.[Cl-].[Na+].O>[N+:1]([C:4]1[CH:13]=[CH:12][C:7]([CH:8]2[CH2:9][O:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 668402-Bromo-4'-nitroacetophenoneHCID 4311764Sodium borohydride

Produkt 1

HCID 922282-(4-Nitrophenyl)oxiraneAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
2.5 °C

Versuchsvorschrift

To an ice-cold stirred suspension of 4-nitrophenacyl bromide (80 g, 0.33 mol) in methanol (800 mL) was added sodium borohydride (13.64 g, 0.36 mol) in small portions. After stirring for 2 h at 0-5° C., potassium carbonate (45.20 g, 0.33 mol) was added in small portions at the same temperature. The suspension was stirred for 18 h at room temperature, diluted with brine (600 mL) and extracted with diethyl ether (600 mL, 500 mL), the combined organic layers were dried over sodium sulfate, filtered and evaporated. The title compound (54.87 g, 0.33 mmol, 100%) was obtained as a pale yellow solid.

Aufarbeitung

  1. stirringThe suspension was stirred for 18 h at room temperature
  2. extractionextracted with diethyl ether (600 mL, 500 mL)
  3. dry with materialthe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-ce75885e707e433d8f5ee23e443ec10f
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372970B2

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