Tetrabutylammonium Fluoride → 3-((4-Ethynyl-1H-pyrazol-1-yl)methyl)-5-methylisoxazole

HRID 2205871Notes

Reaction equation

HRID 2205871 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([CH2:7][N:8]2[CH:12]=[C:11]([C:13]#[C:14][Si](C)(C)C)[CH:10]=[N:9]2)[CH:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.C(OCC)(=O)C.O>[C:13]([C:11]1[CH:10]=[N:9][N:8]([CH2:7][C:4]2[CH:3]=[C:2]([CH3:1])[O:6][N:5]=2)[CH:12]=1)#[CH:14]

Participants

6

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 867062825-Methyl-3-((4-((trimethylsilyl)ethynyl)-1H-pyrazol-1-yl)methyl)isoxazole

Product 1

HCID 867062833-((4-Ethynyl-1H-pyrazol-1-yl)methyl)-5-methylisoxazoleYield 70%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

5-Methyl-3-((4-((trimethylsilyl)ethynyl)-1H-pyrazol-1-yl)methyl)isoxazole (31) (0.55 g, 2.12 mmol) was dissolved in 3 ml THF and stirred at RT. To the stirred solution was then added a 1M solution of TBAF in THF (3 ml, 3 mmol). After 10 minutes, the reaction was diluted with ethyl acetate (20 ml) and water (20 ml). The organic solution was collected, dried and concentrated. The crude product was purified on a short silica column eluting with 5% ethyl acetate in DCM. The pure fractions provided the title compound as a pale brown solid (278 mg, 70%). 1H-NMR (500 MHz, CDCl3) 2.38 (s, 3H), 3 (s, 1H), 5.29 (s, 2H), 5.9 (s, 1H), 7.61 (s, 1H), 7.63 (s, 1H).

Workup

  1. customThe organic solution was collected
  2. customdried
  3. concentrationconcentrated
  4. customThe crude product was purified on a short silica column
  5. washeluting with 5% ethyl acetate in DCM

Sources & evidence

ORD record
ord-86e105a5213c4723b326111c32920666
Source dataset
uspto-grants-2016_06
Patent number
US09371319B2

Reaction notes

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