Triethylamine → Methyl 3-(2-fluorophenyl)-5-methylisoxazole-4-carboxylate

HRID 434028

Reaction equation

HRID 434028 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4](=[N:6][OH:7])Cl.[CH3:12][O:13][C:14](=[O:18])[C:15]#[C:16][CH3:17].CCN(CC)CC>CCOCC>[CH3:12][O:13][C:14]([C:15]1[C:4]([C:3]2[CH:8]=[CH:9][CH:10]=[CH:11][C:2]=2[F:1])=[N:6][O:7][C:16]=1[CH3:17])=[O:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 141019Methyl but-2-ynoateHCID 37581182-fluoro-N-hydroxybenzenecarboximidoyl chloride

Product 1

HCID 18756272Methyl 3-(2-fluorophenyl)-5-methylisoxazole-4-carboxylateYield 58%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

To a solution (0° C., N2) of 2-fluorobenzoylchloride oxime (0.50 g, 2.9 mmol) and methyl-2-butynoate (0.57 g, 5.8 mmol) in Et2O (15 ml) was added a solution of Et3N (0.52 ml) in Et2O (2 ml) over a period of 1 h followed by warming to room temperature while stirring overnight (17 h). The reaction was diluted with Et2O, washed (H2O then brine), dried (MgSO4), filtered, and concentrated. Column chromatography (silica gel, hexanes/EtOAc gradient) gave the title compound (0.39 g, 58%).

Workup

  1. washwashed (H2O
  2. dry with materialbrine), dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8655af1fcd1c4c9a8078c341113f32f9
Source dataset
uspto-grants-2003_12
Patent number
US06670373B1

Linked notes

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