Methanol → HCID 22221378, compound

HRID 1794447Notes

Reaction equation

HRID 1794447 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([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:6][C:7]=1[Cl:8].S(=O)(=O)(O)O.[CH3:24]O>>[Br:1][C:2]1[CH:3]=[C:4]([C:9]2[O:13][N:12]=[CH:11][C:10]=2[CH2:14][CH2:15][C:16]([O:18][CH3:24])=[O:17])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 22221032HCID 22221032, compound

Product 1

HCID 22221378HCID 22221378, compoundYield 78%

Procedure

A mixture of 3-[5-(3-bromo-4-chlorophenyl)-4-isoxazolyl]propionic acid (2.74 g), conc. sulfuric acid (0.2 ml) and methanol (100 ml) was refluxed for 4 hr. The reaction mixture was concentrated, water was added to the residue and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and methyl 3-[5-(3-bromo-4-chlorophenyl)-4-isoxazolyl]propionate (2.22 g, yield 78%) was obtained as colorless crystals from a fraction eluted with ethyl acetate-hexane (1:3, volume ratio). The crystals were recrystallized from ethyl acetate-hexane. melting point: 54–55° C.

Workup

  1. temperaturewas refluxed for 4 hr
  2. concentrationThe reaction mixture was concentrated
  3. additionwater was added to the residue
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with saturated brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2adcc7526b2c4a3b818df54fd931abda
Source dataset
uspto-grants-2006_04
Patent number
US07022725B2

Reaction notes

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