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

HRID 1794438Notes

Reaction equation

HRID 1794438 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[CH:10][C:9]=2[CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH3:23]O>>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:12][N:11]=[CH:10][C:9]=2[CH2:13][CH2:14][C:15]([O:17][CH3:23])=[O:16])=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 222210993-[5-(4-Methylphenyl)-4-isoxazolyl]propionic acid

Product 1

HCID 22221162Methyl 3-[5-(4-methylphenyl)-4-isoxazolyl]propionateYield 79%

Procedure

A mixture of 3-[5-(4-methylphenyl)-4-isoxazolyl]propionic acid (4.00 g), conc. sulfuric acid (2 ml) and methanol (80 ml) was refluxed for 1 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-(4-methylphenyl)-4-isoxazolyl]propionate (3.35 g, yield 79%) was obtained as a colorless oil from a fraction eluted with ethyl acetate-hexane (1:7, volume ratio). NMR (CDCl3) δ: 2.41 (3H, s), 2.63 (2H, t, J=7.5 Hz), 2.99 (2H, t, J=7.5 Hz), 3.68 (3H, s), 7.30 (2H, d, J=8 Hz), 7.59 (2H, d, J=8 Hz), 8.20 (1H, s).

Workup

  1. temperaturewas refluxed for 1 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-122de023205f4aa1a30843962add9f3b
Source dataset
uspto-grants-2006_04
Patent number
US07022725B2

Reaction notes

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