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

HRID 475687Notes

Reaction equation

HRID 475687 reaction equation
[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]

Participants

3

Reactant 2

HCID 10928Ethyl chloroformateHCID 57278894HCID 57278894, compound

Product 1

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

Conditions

Temperature
-78 °C

Procedure

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 Ton. Receiving flasks were cooled to −78° C. to collect the product. Typical distilled yields were approximately 80%.

Workup

  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 Ton
  5. customto collect the product
  6. distillationTypical distilled
  7. customyields

Sources & evidence

ORD record
ord-2c5e560de94a4ecab28bd802fea0e08c
Source dataset
uspto-grants-2014_01
Patent number
US08637614B2

Reaction notes

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