Thionyl Chloride → Ethyl 2-methyl-5-(2-phenylethyl)-1,3-oxazole-4-carboxylate

HRID 1730965Notes

Reaction equation

HRID 1730965 reaction equation
[C:1]([NH:4][CH:5]([C:11](=[O:20])[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=O)[CH3:2].S(Cl)(Cl)=O>>[CH3:2][C:1]1[O:20][C:11]([CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[N:4]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 21417731HCID 21417731, compound

Product 1

HCID 21417734Ethyl 2-methyl-5-(2-phenylethyl)-1,3-oxazole-4-carboxylate

Procedure

1 g. of ethyl 2-acetamido-3-oxo-5-phenylvalerate is dissolved in 4 ml. of thionyl chloride, and the solution heated for 15 minutes. The reaction mixture is then evaporated under vacuum to obtain a residue which is then washed with 10 ml. of 5% aqueous sodium bicarbonate solution, then extracted twice with 25 ml. of methylene chloride. The combined extracts are then evaporated under vacuum to obtain ethyl 2-methyl-5-phenethyl-4-oxazolecarboxylate as an oil.

Workup

  1. customThe reaction mixture is then evaporated under vacuum
  2. customto obtain a residue which
  3. washis then washed with 10 ml
  4. extractionof 5% aqueous sodium bicarbonate solution, then extracted twice with 25 ml
  5. customThe combined extracts are then evaporated under vacuum

Sources & evidence

ORD record
ord-89860c78f7dd469ba08efee203725c92
Source dataset
uspto-grants-1976_11
Patent number
US03994915

Reaction notes

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