Ethyl chloroformate → 2-Ethenyl-4,4-dimethyl-1,3-oxazol-5(4H)-one

HRID 452282Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 452282
[C:1]([CH2:5][NH:6][C@H:7]([C:9]([OH:11])=[O:10])[CH3:8])(=O)[CH:2]=C.Cl[C:13](OCC)=O>>[CH3:13][C:7]1([CH3:8])[N:6]=[C:5]([CH:1]=[CH2:2])[O:10][C:9]1=[O:11]

Komponenten

3

Edukt 2

HCID 10928Ethyl chloroformateHCID 57278894HCID 57278894, Verbindung

Produkt 1

HCID 98127942-Ethenyl-4,4-dimethyl-1,3-oxazol-5(4H)-one

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

2-Vinyl-4,4-Dimethylazlactone (VDM) was prepared from N-acryloylmethylalanine (S. M. Heilmann and H. K. Smith II, J. Appl. Polym. Sci., 24, 1551 (1979)) by the Taylor and Platt procedure (L. D. Taylor and T. E. Platt, J. Polym. Sci. Polym. Lett. Ed., 7, 597 (1969)) with ethyl chloroformate as the dehydrating agent. A modified workup procedure was used in which, instead of cooling the filtrate to crystallize the product, the filtrate was concentrated on a rotary evaporator, and the crude product was distilled just above room temperature at 0.5 Torr. Receiving flasks were cooled to −78° C. to collect the product. Typical distilled yields were approximately 80%.

Aufarbeitung

  1. temperatureinstead of cooling the filtrate
  2. customto crystallize the product
  3. concentrationthe filtrate was concentrated on a rotary evaporator
  4. distillationthe crude product was distilled just above room temperature at 0.5 Torr
  5. customto collect the product
  6. distillationTypical distilled
  7. customyields

Quellen und Nachweise

ORD-Eintrag
ord-60b61a9f78fc43a9ac1283bfb1c25cc0
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08491749B2

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