Methanol → HCID 22221271, compound

HRID 1794417Notes

Reaction equation

HRID 1794417 reaction equation
[Cl: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[F:8].S(=O)(=O)(O)O.[CH3:24]O>>[Cl: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[F:8]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 22221113HCID 22221113, compound

Product 1

HCID 22221271HCID 22221271, compoundYield 97%

Procedure

A mixture of 3-[5-(3-chloro-4-fluorophenyl)-4-isoxazolyl]propionic acid (3.10 g), conc. sulfuric acid (0.1 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-chloro-4-fluorophenyl)-4-isoxazolyl]propionate (3.18 g, yield 97%) was obtained as a pale yellow oil from a fraction eluted with ethyl acetate-hexane (1:3, volume ratio). NMR (CDCl3) δ: 2.60–2.72 (2H, m), 2.91–3.03 (2H, m), 3.69 (3H, s), 7.22–7.33 (1H, m), 7.52–7.66 (1H, m), 7.74–7.82 (1H, m), 8.23 (1H, s).

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-81742a96fdb14e7e9050b0ef5e1283d6
Source dataset
uspto-grants-2006_04
Patent number
US07022725B2

Reaction notes

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