Tetrabutylammonium Fluoride → 2,6-Dipropyl-4-vinylphenol

HRID 865519

Reaction equation

HRID 865519 reaction equation
[Si]([O:8][C:9]1[C:14]([CH2:15][CH2:16][CH3:17])=[CH:13][C:12]([CH:18]=[CH2:19])=[CH:11][C:10]=1[CH2:20][CH2:21][CH3:22])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.CCOCC.C(OCC)(=O)C>C1COCC1>[CH2:15]([C:14]1[CH:13]=[C:12]([CH:18]=[CH2:19])[CH:11]=[C:10]([CH2:20][CH2:21][CH3:22])[C:9]=1[OH:8])[CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 19080390t-Butyldimethylsilyloxy-2,6-dipropyl-4-vinyl benzeneHCID 21584169Diethylether ethylacetate

Product 1

HCID 184004142,6-Dipropyl-4-vinylphenol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared from t-butyldimethylsilyloxy-2,6-dipropyl-4-vinylbenzene (Step B, Example 14) by treatment with tetrabutylammonium fluoride in THF for a few hours. It was poured into ether/ethyl acetate mixture and washed with brine. After removal of the solvent the crude product was purified by flash column chromatography using ethyl acetate/hexane as eluent.

Workup

  1. washwashed with brine
  2. customAfter removal of the solvent the crude product
  3. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-b691e006f5a44a418b5d734b63087261
Source dataset
uspto-grants-1996_10
Patent number
US05565485

Linked notes

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