Dimethyl Sulfide → Propyl 3-oxocyclobutanecarboxylate

HRID 1412352Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1412352
[O:1]=[O+][O-].C=[C:5]1[CH2:8][CH:7]([C:9]([O:11][CH2:12][CH2:13][CH3:14])=[O:10])[CH2:6]1.CSC>CO>[O:1]=[C:5]1[CH2:8][CH:7]([C:9]([O:11][CH2:12][CH2:13][CH3:14])=[O:10])[CH2:6]1

Komponenten

5

Edukt 3

HCID 1068Dimethyl SulfideHCID 24823OzoneHCID 45090160Cyclobutanecarboxylic acid, 3-methylene-, propyl ester

Produkt 1

HCID 67008885Propyl 3-oxocyclobutanecarboxylateAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

An ozone gas was blown into a solution (200 mL) of propyl 3-methylidenecyclobutanecarboxylate (15 g) in methanol at −78° C. for 2 hr. Dimethyl sulfide (21 g) was added to the reaction mixture at the same temperature, and the mixture was warmed to room temperature over 1 hr. The obtained mixture was concentrated and purified by silica gel column chromatography to give the title compound as a colorless oil (13 g, 88%).

Aufarbeitung

  1. concentrationThe obtained mixture was concentrated
  2. custompurified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-839f56b571a84a5cb299b95c7ba54fa6
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921379B2

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