Dimethylformamide → Methyl 3-(3-fluoro-2-hydroxypropoxy)isoxazole-5-carboxylate

HRID 1026279Notes

Reaction equation

HRID 1026279 reaction equation
[OH:1][C:2]1[CH:6]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[O:4][N:3]=1.[F:11][CH2:12][CH:13]1[CH2:15][O:14]1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[F:11][CH2:12][CH:13]([OH:14])[CH2:15][O:1][C:2]1[CH:6]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[O:4][N:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 104181,2-Epoxy-3-fluoropropaneHCID 11430Potassium CarbonateHCID 178498603HCID 178498603, compound

Product 1

HCID 67778586Methyl 3-(3-fluoro-2-hydroxypropoxy)isoxazole-5-carboxylateYield 20.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl 3-hydroxyisoxazole-5-carboxylate (1.88 g), 2-(fluoromethyl)oxirane (1.00 g), potassium carbonate (1.82 g) and DMF (2 mL) was stirred at room temperature for 2 hr, and then at 70° C. overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound as a white powder (585 mg).

Workup

  1. customat 70° C.
  2. customovernight
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe obtained organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-3d3184b8ecaf47eea6539dc31b83b13a
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

Loading…