Tetrabutylammonium Fluoride → 1-Ethynyl-1-(trifluoromethyl)but-3-en-1-yl 4-nitrobenzoate

HRID 2422502Notes

Reaction equation

HRID 2422502 reaction equation
[N+:1]([C:4]1[CH:32]=[CH:31][C:7]([C:8]([O:10][C:11]([C:27]([F:30])([F:29])[F:28])([C:15]#[C:16][Si](C(C)C)(C(C)C)C(C)C)[CH2:12][CH:13]=[CH2:14])=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([O:10][C:11]([C:15]#[CH:16])([C:27]([F:28])([F:29])[F:30])[CH2:12][CH:13]=[CH2:14])=[O:9])=[CH:31][CH:32]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59774863HCID 59774863, compound

Product 1

HCID 597748961-Ethynyl-1-(trifluoromethyl)but-3-en-1-yl 4-nitrobenzoateYield 25.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of crude 1-(trifluoromethyl)-1-[(triisopropylsilyl)ethynyl]but-3-en-1-yl 4-nitrobenzoate from Step 2 (˜0.755 mmol) in THF (3 mL) at room temperature was added a THF solution of tetrabutylammonium fluoride (1.0 M, 0.906 mL, 0.906 mmol). After 2.5 h the reaction mixture was poured in H2O and extracted with EtOAc (3×). The combined organic layers were washed with H2O and brine, dried (Na2SO4) and concentrated. The residue was subjected to chromatography on silica gel (toluene/hexane 40:60 to 60:40) affording the title compound (60 mg). 1H NMR (500 MHz, acetone-d6): 8.44 (d, 2H), 8.29 (d, 2H), 5.94 (m, 1H), 5.29 (d, 1H), 5.21 (d, 1H), 3.74 (s, 1H), 3.27 (m, 2H).

Workup

  1. extractionextracted with EtOAc (3×)
  2. washThe combined organic layers were washed with H2O and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0db8869a0e6b405dbbd2be275d633f1e
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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