Potassium Hydroxide → 5-Ethoxy-4-methyl-2-vinyloxazole

HRID 972846Notes

Reaction equation

HRID 972846 reaction equation
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[CH2:15]([O:17][C:18](=[O:26])[C@H:19]([CH3:25])[NH:20][C:21](=O)[CH:22]=[CH2:23])[CH3:16].[OH-].[K+]>C(Cl)(Cl)Cl>[CH2:15]([O:17][C:18]1[O:26][C:21]([CH:22]=[CH2:23])=[N:20][C:19]=1[CH3:25])[CH3:16]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 14812Phosphorus oxide (P4O10)HCID 54390476N-acryloylalanine ethyl ester

Product 1

HCID 202639815-Ethoxy-4-methyl-2-vinyloxazole

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a suspension of 1.0 mole of phosphorous pentoxide in 300 ml. of dry chloroform is added dropwise with stirring a solution of 0.5 mole of N-acryloylalanine ethyl ester. The reaction mixture is heated at gentle reflux for 5 hours and then cooled. To the cooled mixture is added with rapid stirring 750 ml. of 20% aqueous potassium hydroxide. After stirring at room temperature for 1 hour, the chloroform layer is separated and the aqueous layer extracted with 2 × 200 ml. of chloroform. The combined chloroform extracts are washed with water, dried over sodium sulfate, and concentrated in vacuo to yield 5-ethoxy-4-methyl-2-vinyloxazole.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat gentle reflux for 5 hours
  3. temperaturecooled
  4. additionTo the cooled mixture is added
  5. stirringAfter stirring at room temperature for 1 hour
  6. customthe chloroform layer is separated
  7. extractionthe aqueous layer extracted with 2 × 200 ml
  8. washThe combined chloroform extracts are washed with water
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a7d0be47d79f468781795f1644778f80
Source dataset
uspto-grants-1977_10
Patent number
US04053606

Reaction notes

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