Methanol → HCID 22221223, compound

HRID 1794399Notes

Reaction equation

HRID 1794399 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]2[O:11][N:10]=[CH:9][C:8]=2[CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH3:22]O>>[Cl:1][C:2]1[S:6][C:5]([C:7]2[O:11][N:10]=[CH:9][C:8]=2[CH2:12][CH2:13][C:14]([O:16][CH3:22])=[O:15])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 22220991HCID 22220991, compound

Product 1

HCID 22221223HCID 22221223, compoundYield 86%

Procedure

To a solution of 3-[5-(5-chloro-2-thienyl)-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, iced water was poured on the residue and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and crystals (3.80 g, yield 86%) of methyl 3-[5-(5-chloro-2-thienyl)-4-isoxazolyl]propionate were obtained from a fraction eluted with ethyl acetate-hexane (1:3, volume ratio). The crystals were recrystallized from diethyl ether-isopropyl ether to give a colorless prism. melting point: 34–35° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hr
  3. concentrationThe reaction mixture was concentrated
  4. additioniced water was poured on the residue
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with water
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-90b981e05e894b8eb303caf17a82b4f6
Source dataset
uspto-grants-2006_04
Patent number
US07022725B2

Reaction notes

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