Reaktion #90496

ord-2aa6503ec8d54b4c92015055e89bae7a

Reaktionsgleichung

CCO
EtOH
CC(=O)CC(C)=O
Acetylacetone
CCOC([O-])[O-]
Ethyl orthoformate
CC(=O)OC(C)=O
Acetic anhydride
→
CCOC=C(C(C)=O)C(C)=O
title compound
Ausbeute 17.0%
CCOC=C(C(C)=O)C(C)=O
3-(ethoxymethylene)pentane-2,4-dione
Ausbeute 17.0%

Edukte

CCO
EtOH
CC(=O)CC(C)=O
Acetylacetone
CCOC([O-])[O-]
Ethyl orthoformate
CC(=O)OC(C)=O
Acetic anhydride

Reagenzien

Keine

Lösungsmittel

CCOC(C)=O
EtOAc
CCOC(C)=O
EtOAc

Reaktionsbedingungen

Temperatur
150°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    TemperaturThe reaction solution was cooled to room temperature
  2. 2
    workup.ADDITIONConcentration of the fractions containing the pure product
  3. 3
    Sonstigeat 40° C.

Vorschrift

A solution of Acetylacetone (40 mL), Ethyl orthoformate (95.4 mL) and Acetic anhydride (54.2 mL) was heated to reflux (150° C.) for 1 hour. The reaction solution was cooled to room temperature and was directly subjected to flash column chromatography (E. Merck Silica Gel (˜120 g); Eluent: 100% EtOAc followed by 5% EtOH in EtOAc). Concentration of the fractions containing the pure product using a rotavap at 40° C. afforded the title compound as a dark red viscous oil (10.4 g, 17.0%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09446046B2uspto-grants-2016_09