Methanol → HCID 22221290, compound

HRID 1794440Notes

Reaction equation

HRID 1794440 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:12][N:11]=[CH:10][C:9]=2[CH2:13][CH2:14][C:15]([OH:17])=[O:16])[S:5][C:6]=1[Cl:7].S(=O)(=O)(O)O.[CH3:23]O>>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:12][N:11]=[CH:10][C:9]=2[CH2:13][CH2:14][C:15]([O:17][CH3:23])=[O:16])[S:5][C:6]=1[Cl:7]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 22221159HCID 22221159, compound

Product 1

HCID 22221290HCID 22221290, compoundYield 80%

Procedure

To a solution of 3-[5-(4,5-dichloro-2-thienyl)-4-isoxazolyl]propionic acid (1.60 g) in methanol (30 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 saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and crystals (1.34 g, yield 80%) of methyl 3-[5-(4,5-dichloro-2-thienyl)-4-isoxazolyl]propionate was obtained from a fraction eluted with ethyl acetate-hexane (1:7, volume ratio). The crystals were recrystallized from diethyl ether-hexane to give a colorless needle. melting point: 49–50° 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 saturated brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-189d802618ad4f2eb8c109e22bd12c6f
Source dataset
uspto-grants-2006_04
Patent number
US07022725B2

Reaction notes

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