Dimethyl Sulfide → 2-Methyl-4-oxo-4H-chromene-8-carbaldehyde

HRID 557390Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 557390
[CH3:1][C:2]1[O:3][C:4]2[C:9]([C:10](=[O:12])[CH:11]=1)=[CH:8][CH:7]=[CH:6][C:5]=2/[CH:13]=C/C.[O:16]=[O+][O-].CSC>ClCCl>[CH3:1][C:2]1[O:3][C:4]2[C:9]([C:10](=[O:12])[CH:11]=1)=[CH:8][CH:7]=[CH:6][C:5]=2[CH:13]=[O:16]

Komponenten

5

Edukt 3

HCID 1068Dimethyl SulfideHCID 24823OzoneHCID 574388872-Methyl-8-[(1E)-prop-1-en-1-yl]-4H-chromen-4-one

Produkt 1

HCID 133748832-Methyl-4-oxo-4H-chromene-8-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-60 °C

Versuchsvorschrift

18.5 g (62.8 mmol) of 2-methyl-8-[(1E)-prop-1-en-1-yl]-4H-chromen-4-one are dissolved in 400 ml of dichloromethane and cooled to −60° C. Ozone is passed into the reaction solution for 30 min. Dimethyl sulfide is then added to the reaction mixture. After warming to room temperature, the solvent is removed in vacuo, and the residue is slurried in a little methanol. The solid remaining after filtration is recrystallized from diethyl ether. 9.1 g (77.4% of theory) of the title compound are obtained.

Aufarbeitung

  1. temperatureAfter warming to room temperature
  2. customthe solvent is removed in vacuo
  3. filtrationafter filtration
  4. customis recrystallized from diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-5dc37c69728d495e9667d0815d48ea58
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08058447B2

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