Tetrabutylammonium Fluoride → 3-Cyclopropylphenol

HRID 2363108Notes

Reaction equation

HRID 2363108 reaction equation
C([Si]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]2[CH2:17][CH2:16]2)[CH:10]=1)(C)C)(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.CCOC(C)=O.O>[CH:15]1([C:11]2[CH:10]=[C:9]([OH:8])[CH:14]=[CH:13][CH:12]=2)[CH2:17][CH2:16]1

Participants

6

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 58319284HCID 58319284, compound

Product 1

HCID 201000043-CyclopropylphenolYield 95%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl-(3-cyclopropyl-phenoxy)-dimethyl-silane (390 mg, 1.57 mmol) in THF (5 mL) was added a solution of 1M-TBAF (in THF, 2 mL, 1.3 mmol), and the mixture was stirred for 30 min at room temperature. The residue was diluted with EtOAc and water. The organic layer was washed with saturated ammonium chloride, water and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by column chromatography to give 3-cyclopropyl-phenol (200 mg, 95%).

Workup

  1. washThe organic layer was washed with saturated ammonium chloride, water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude residue was purified by column chromatography

Sources & evidence

ORD record
ord-826d3935ac5445a1b471234981e6afa6
Source dataset
uspto-grants-2014_04
Patent number
US08691855B2

Reaction notes

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