Sodium hydride → 2-[4-(Benzyloxy)phenyl]oxirane

HRID 75146

Reaktionsgleichung

Reaktionsgleichung von HRID 75146
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[CH2:9]([O:16][C:17]1[CH:24]=[CH:23][C:20]([CH:21]=[O:22])=[CH:19][CH:18]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CS(C)=O.C1COCC1>[CH2:9]([O:16][C:17]1[CH:18]=[CH:19][C:20]([CH:21]2[CH2:4][O:22]2)=[CH:23][CH:24]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 78109Benzaldehyde, 4-(phenylmethoxy)-

Produkt 1

HCID 132487172-[4-(Benzyloxy)phenyl]oxirane

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

NaH (60%, 0.5 g, 23.6 mmol) was diluted in DMSO (50 mL) and stirred for 30 min at rt under nitrogen. Trimethylsulfoxonium iodide (7.8 g, 35.37 mmol) was added in portions at 0° C. The reaction mixture was stirred for 1 h. Then a solution of 4-benzyloxybenzaldehyde (5 g, 23.58 mmol) in THF (15 mL) was added. The reaction solution was stirred at rt for 3 h. The reaction mixture was poured into ice-water and extracted with ether. The organic layer was dried over Na2SO4 and concentrated to give 2-(4-(benzyloxy)phenyl)oxirane, which was used for the next step without further purification.

Aufarbeitung

  1. stirringThe reaction mixture was stirred for 1 h
  2. stirringThe reaction solution was stirred at rt for 3 h
  3. extractionextracted with ether
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-f83472feade14f389d273c03cc1e6dd5
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835426B2

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