Tetrabutylammonium Fluoride → beta-Methylenephenethyl alcohol

HRID 77326

Reaction equation

HRID 77326 reaction equation
C([Si](C)(C)[O:6][CH2:7][C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[CH2:9])(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:10]1([C:8](=[CH2:9])[CH2:7][OH:6])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67155247tert-Butyl-dimethyl-(2-phenyl-allyloxy)-silane

Product 1

HCID 80106beta-Methylenephenethyl alcoholYield 99.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a well stirred solution of tert-butyl-dimethyl-(2-phenyl-allyloxy)-silane (1.3 g, 5.23 mmol) in tetrahydrofuran (10 mL) is slowly added a solution of a 1 N tetrabutylammonium fluoride in tetrahydrofuran (10.5 mL, 10.5 mmol). The reaction is allowed to stir for 20 min, quenched by the addition of a saturated aqueous solution of ammonium chloride and extracted several times with ethyl acetate The organic layers are combined, washed with water, brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue is purified via silica gel chromatography (10% ethyl acetate in hexanes) to yield 700 mg of the title compound.

Workup

  1. customquenched by the addition of a saturated aqueous solution of ammonium chloride
  2. extractionextracted several times with ethyl acetate The organic layers
  3. washwashed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified via silica gel chromatography (10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-040cf4c5b67048c3a151c517cf90500a
Source dataset
uspto-grants-2014_09
Patent number
US08841291B2

Linked notes

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