Hydrochloric Acid → Methyl 3-[4-(4-chlorophenyl)-2-methyl-1,3-oxazol-5-yl]propanoate

HRID 1982439Notes

Reaction equation

HRID 1982439 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH3:18])[O:11][C:12]=2[CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[CH:4][CH:3]=1.Cl.[CH3:20]O>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([CH3:18])[O:11][C:12]=2[CH2:13][CH2:14][C:15]([O:17][CH3:20])=[O:16])=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 132932823-[4-(4-Chlorophenyl)-2-methyl-1,3-oxazol-5-yl]propanoic acid

Product 1

HCID 13293290Methyl 3-[4-(4-chlorophenyl)-2-methyl-1,3-oxazol-5-yl]propanoate

Procedure

A mixture of 4-(4-chlorophenyl)-2-methyloxazole-5-propionic acid (10.0 g), methanol (50 ml) and 20% methanolic hydrogen chloride (50 ml) was allowed to stand at room temperature for 2 hours. The solvent was distilled off, followed by addition of water. The mixture was neutralized with potassium carbonate and extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was then distilled off and the residue was further distilled under reduced pressure to give crystals of methyl 4-(4-chlorophenyl)-2-methyloxazole-5-propionate, yield 7.7 g (68.8%), b.p. 162° C./0.7 mmHg, m.p. 74°-75° C.

Workup

  1. distillationThe solvent was distilled off
  2. additionfollowed by addition of water
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was then distilled off
  7. distillationthe residue was further distilled under reduced pressure

Sources & evidence

ORD record
ord-49902c8c69f04392b2941b5c95c3b9d3
Source dataset
uspto-grants-1986_06
Patent number
US04596816

Reaction notes

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