Methanol → HCID 22221082, compound

HRID 1794395Notes

Reaction equation

HRID 1794395 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[O:13][N:12]=[CH:11][C:10]=1[CH2:14][CH2:15][C:16]([OH:18])=[O:17].S(=O)(=O)(O)O.[CH3:24]O>>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[O:13][N:12]=[CH:11][C:10]=1[CH2:14][CH2:15][C:16]([O:18][CH3:24])=[O:17]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 22221141HCID 22221141, compound

Product 1

HCID 22221082HCID 22221082, compoundYield 87%

Procedure

To a solution of 3-[5-(2,4-difluorophenyl)-4-isoxazolyl]propionic acid (1.25 g) in methanol (40 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 were collected by filtration. The crystals were subjected to silica gel column chromatography, and the crystals obtained from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio) were recrystallized from ethyl acetate-hexane to give a colorless prism (1.15 g, yield 87%) of methyl 3-[5-(2,4-difluorophenyl)-4-isoxazolyl]propionate. melting point: 40–41° 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
  5. filtrationThe precipitated crystals were collected by filtration
  6. customthe crystals obtained from a fraction
  7. washeluted with ethyl acetate-hexane (1:1, volume ratio)
  8. customwere recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-b0b9b98902f8450cae7b1be3d892529b
Source dataset
uspto-grants-2006_04
Patent number
US07022725B2

Reaction notes

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