Triethylamine → Ethyl 5-[3-(trifluoromethyl)phenyl]-1,2-oxazole-3-carboxylate

HRID 1694640Notes

Reaction equation

HRID 1694640 reaction equation
[CH3:1][CH2:2][O:3][C:4](/[C:6](/Cl)=[N:7]\[OH:8])=[O:5].[F:10][C:11]([F:21])([F:20])[C:12]1[CH:13]=[C:14]([C:18]#[CH:19])[CH:15]=[CH:16][CH:17]=1.C(N(CC)CC)C>O1CCCC1>[F:10][C:11]([F:20])([F:21])[C:12]1[CH:13]=[C:14]([C:18]2[O:8][N:7]=[C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[CH:19]=2)[CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27784901-Ethynyl-3-(trifluoromethyl)benzeneHCID 6399471Ethyl 2-chloro-2-(hydroxyimino)acetate

Product 1

HCID 53439058Ethyl 5-[3-(trifluoromethyl)phenyl]-1,2-oxazole-3-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ethyl chlorooximidoacetate (6.68 g, 44.09 mmol) in tetrahydrofuran (90 mL) in an ice bath was added 3-(trifluoromethyl)phenylacetylene (5.0 g, 29.39 mmol) slowly, followed by triethylamine (8.19 mL, 58.78 mmol) dropwise. The resulting mixture was stirred at room temperature overnight, which was then filtered through a layer of silica gel (top) and anhydrous Na2SO4 (bottom), and washed with ethyl acetate. The filtrate was washed with water, the organic layer dried over sodium sulfate, and the solvent removed under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:Hexanes=1:9) to afford ethyl 5-[3-(trifluoromethyl)phenyl]isoxazole-3-carboxylate.

Workup

  1. filtrationwhich was then filtered through a layer of silica gel (top) and anhydrous Na2SO4 (bottom)
  2. washwashed with ethyl acetate
  3. washThe filtrate was washed with water
  4. dry with materialthe organic layer dried over sodium sulfate
  5. customthe solvent removed under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate:Hexanes=1:9)

Sources & evidence

ORD record
ord-7cd9aff82f6c4b5691c6a34e63a593b1
Source dataset
uspto-grants-2012_04
Patent number
US08158810B2

Reaction notes

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