Triethylamine → 3-(Trifluoromethyl)isoxazole

HRID 240809

Reaction equation

HRID 240809 reaction equation
C1(N=C=O)C=CC(N=C=O)=CC=1.C(N(CC)CC)C.COC1C=C[C:25]([C:28]#[C:29][C:30]([F:33])([F:32])[F:31])=CC=1.COC(=O)CCC[N+:40]([O-])=[O:41]>C1(C)C=CC=CC=1>[F:31][C:30]([C:29]1[CH:28]=[CH:25][O:41][N:40]=1)([F:33])[F:32]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 25604Methyl 4-nitrobutyrateHCID 610091,4-DiisocyanatobenzeneHCID 11333117Benzene, 1-methoxy-4-(3,3,3-trifluoro-1-propynyl)-

Product 1

HCID 137394013-(Trifluoromethyl)isoxazoleYield 56.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
150 °C

Procedure

1,4-Phenylene diisocyanate (597.1 mg, 3.73 mol) and triethylamine (780 μL, 5.60 mmol) were added to a solution of 1-methoxy-4-trifluoropropynylbenzene (373.2 mg, 1.86 mmol) and 4-nitrobutanoic acid methyl ester (441.5 mg, 2.80 mmol) in toluene (10 mL). Using a microwave reactor, the obtained mixture was stirred at 150° C. for 2 hours. The reaction solution was filtered with celite, and the solvent was then distilled away. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain a trifluoromethyl isoxazole compound (144.0 mg, yield: 25%).

Workup

  1. filtrationThe reaction solution was filtered with celite
  2. distillationthe solvent was then distilled away
  3. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-2e26deebd655408b90e6dec23afdcba7
Source dataset
uspto-grants-2014_02
Patent number
US08648103B2

Linked notes

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