Methanol → Methyl 3-[5-(4-trifluoromethylphenyl)-4-isoxazolyl]propionate

HRID 1794394Notes

Reaction equation

HRID 1794394 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][N:12]=[CH:11][C:10]=2[CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[CH:5][CH:4]=1.S(=O)(=O)(O)O.[CH3:26]O>>[F:20][C:2]([F:1])([F:19])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][N:12]=[CH:11][C:10]=2[CH2:14][CH2:15][C:16]([O:18][CH3:26])=[O:17])=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 222214183-[5-(4-Trifluoromethylphenyl)-4-isoxazolyl]propionic acid

Product 1

HCID 22221371Methyl 3-[5-(4-trifluoromethylphenyl)-4-isoxazolyl]propionateYield 74%

Procedure

To a solution of 3-[5-(4-trifluoromethylphenyl)-4-isoxazolyl]propionic acid (2.20 g) in methanol (50 ml) was added conc. sulfuric acid (1 ml) and the mixture was heated under reflux for 1 hr. The reaction mixture was concentrated, and iced water was poured into the residue. The precipitated crystals (1.70 g, yield 74%) of methyl 3-[5-(4-trifluoromethylphenyl)-4-isoxazolyl]propionate were collected by filtration. The crystals were recrystallized from ethyl acetate-hexane to give a colorless prism. melting point: 68–69° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hr
  3. concentrationThe reaction mixture was concentrated
  4. additioniced water was poured into the residue

Sources & evidence

ORD record
ord-b30626f3a600444d9f93d1c4d6f16a3b
Source dataset
uspto-grants-2006_04
Patent number
US07022725B2

Reaction notes

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