Dimethyl Sulfoxide → 2-(4-Methoxyphenyl)oxirane

HRID 596612

Reaktionsgleichung

Reaktionsgleichung von HRID 596612
[H-].[Na+].CS(C)=O.[I-].[CH3:8][S+](C)C.[CH3:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=1>O.O1CCCC1>[CH3:12][O:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]2[O:19][CH2:8]2)=[CH:16][CH:15]=1

Komponenten

7

Edukt 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 312444-MethoxybenzaldehydeHCID 75127Trimethylsulfonium iodide

Produkt 1

HCID 980482-(4-Methoxyphenyl)oxirane

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-5 °C

Versuchsvorschrift

A suspension of 4.84 g. of sodium hydride (57% mineral oil dispersion) in 70 ml. of dry dimethyl sulfoxide is heated at about 65° C. under argon with stirring for 1 hour. Dry tetrahydrofuran (75 ml.) is added and the resulting solution is cooled to -5° C. Trimethylsulfonium iodide (19 g., 92.8 mmol) is added very slowly and stirring is continued for about 5 minutes. A solution of 12.6 g. (92.8 mmol) of p-methoxybenzaldehyde in 120 ml. of tetrahydrofuran is added and the temperature is maintained at -5° C. After addition is completed the mixture is allowed to warm to room temperature, poured into water and extracted with ether. The extract is washed with saturated sodium chloride solution, dried and evaporated to give p-methoxystyrene oxide.

Aufarbeitung

  1. additionA suspension of 4.84 g
  2. stirringstirring
  3. waitis continued for about 5 minutes
  4. temperaturethe temperature is maintained at -5° C
  5. additionAfter addition
  6. temperatureto warm to room temperature
  7. extractionextracted with ether
  8. washThe extract is washed with saturated sodium chloride solution
  9. customdried
  10. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-4da0328f32a445f8b0a12e1ec02d976a
Quelldatensatz
uspto-grants-1977_03
Patentnummer
US04011319

Verknüpfte Notizen

Wird geladen…