Tetrabutylammonium Fluoride → HCID 59774877, compound

HRID 2422499Notes

Reaction equation

HRID 2422499 reaction equation
[N+:1]([C:4]1[CH:32]=[CH:31][C:7]([C:8]([O:10][C:11]([CH:28]2[CH2:30][CH2:29]2)([C:24]([F:27])([F:26])[F:25])[C:12]#[C:13][Si](C(C)C)(C(C)C)C(C)C)=[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]([CH:28]2[CH2:29][CH2:30]2)([C:24]([F:25])([F:26])[F:27])[C:12]#[CH:13])=[O:9])=[CH:31][CH:32]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59774912HCID 59774912, compound

Product 1

HCID 59774877HCID 59774877, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of crude 1-cyclopropyl-1-(trifluoromethyl)-3-(triisopropylsilyl)prop-2-yn-1-yl 4-nitrobenzoate from Step 3 (˜8.14 mmol) in THF (30 mL) at room temperature was added a THF solution of tetrabutylammonium fluoride (1.0 M, 9.77 mL, 9.77 mmol). After 1.5 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. 1H NMR (400 MHz, acetone-d6): 8.44 (d, 2H), 8.29 (d, 2H), 3.64 (s, 1H), 1.53 (m, 1H), 1.26 (m, 1H), 0.88 (m, 2H), 0.78 (m, 1H).

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-c013035ebe85499a89a0cab34d8ecd40
Source dataset
uspto-grants-2011_06
Patent number
US07960409B2

Reaction notes

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