Oxygen → Tert-Butyl 1-(2-oxoethyl)cyclopropanecarboxylate

HRID 238170Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 238170
[CH2:1]([C:4]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5]1)[CH:2]=C.[O:14]=[O+][O-].O=O.CSC>CO.ClCCl>[O:14]=[CH:2][CH2:1][C:4]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5]1

Komponenten

7

Edukt 4

HCID 977OxygenHCID 1068Dimethyl SulfideHCID 24823Ozone2×HCID 546367Cyclopropanecarboxylic acid, 1-(2-propenyl)-, 1,1-dimethylethyl ester

Produkt 1

HCID 58817571Tert-Butyl 1-(2-oxoethyl)cyclopropanecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

4.0 g (21.9 mmol) of tert-butyl 1-(prop-2-en-1-yl)cyclopropanecarboxylate were dissolved in 70 ml of methanol and 30 ml of dichloromethane. At −78° C., ozone in a stream of O2 was passed through the reaction solution for 45 min using an ozone generator. Once the color of the solution had changed to light blue, the reaction solution was flushed with pure oxygen until the color had disappeared again. 6.5 ml (88.9 mmol) of dimethyl sulfide were then added, and the reaction solution was slowly warmed to RT. The mixture was concentrated on a rotary evaporator and the residue was purified by chromatography on silica gel (mobile phase gradient cyclohexane/ethyl acetate 50:1, 30:1, 20:1, 10:1). This gave 1.87 g (44.1% of theory) of the target compound.

Aufarbeitung

  1. customwas flushed with pure oxygen until the color
  2. concentrationThe mixture was concentrated on a rotary evaporator
  3. customthe residue was purified by chromatography on silica gel (mobile phase gradient cyclohexane/ethyl acetate 50:1, 30:1, 20:1, 10:1)

Quellen und Nachweise

ORD-Eintrag
ord-207b2a0e02ac43db874ec8f41379d8dc
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642592B2

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