Dimethyl Sulfide → HCID 21476898, Verbindung

HRID 2293581Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2293581
[CH2:1]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=1[CH:14]=C)[C:7]([O:9][CH3:10])=[O:8])[CH2:2][CH3:3].[O:16]=[O+][O-].CSC>CO.C(Cl)Cl>[CH:14]([C:13]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][C:4]=1[CH2:1][CH2:2][CH3:3])=[O:16]

Komponenten

6

Edukt 3

HCID 1068Dimethyl SulfideHCID 24823Ozone3×HCID 21476907HCID 21476907, Verbindung

Produkt 1

HCID 21476898HCID 21476898, VerbindungAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a magnetically stirred solution of 2.796 g (14.0 mmol) of the product of Step B dissolved in a mixture of 15 mL methanol and 5 mL methylene chloride was introduced a slow stream of ozone at -78° C. After 15 minutes a persistent blue color of excess ozone was observed and the flow of ozone was stopped. Excess methylsulfide (2 mL) was added via syringe, the reaction mixture was allowed to warm to room temperature, and stirring was continued for 12 hours. The reaction mixture was then concentrated on a rotary evaporator and then purified on a silica gel flash chromatography column eluted with 5% EtOAc-hexane. Evaporation of the purified fractions and drying in vacuo afforded 1.677 g (59%) of the title compound as a clear oil.

Aufarbeitung

  1. concentrationThe reaction mixture was then concentrated on a rotary evaporator
  2. custompurified on a silica gel flash chromatography column
  3. washeluted with 5% EtOAc-hexane
  4. customEvaporation of the purified fractions
  5. customdrying in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-84124b06bf244c98a82125e7aaa1eae5
Quelldatensatz
uspto-grants-1997_11
Patentnummer
US05686478

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