Tetrabutylammonium Fluoride → 4-Hydroxy-3-(2-propen-1-yl)benzyl alcohol

HRID 2255636Notes

Reaction equation

HRID 2255636 reaction equation
[Si]([O:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][OH:14])=[CH:11][C:10]=1[CH2:17][CH:18]=[CH2:19])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][OH:14])=[CH:11][C:10]=1[CH2:17][CH:18]=[CH2:19]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 544131774-(Tert-butyldimethylsilyloxy)3-(2-propen-1-yl)benzyl alcohol

Product 1

HCID 539952564-Hydroxy-3-(2-propen-1-yl)benzyl alcoholYield 793.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of approximately 7.26 g (2.6 mmol) of crude 4-tert-butyldimethylsilyloxy-3-(prop-2-enyl)benzyl alcohol (Step D of Example 42) dissolved in 50 mL of anhydrous THF was added 26 mL (2.6 mmol) of tetra-n-butylammonium fluoride and the reaction mixture was stirred at room temperature for 16 hours. The mixture was then evaporated in vacuo and the residual oil was purified on a silica gel flash chromatography column eluted with 5% methanol/chloroform to afford 3.386 g (79%) of the title compound as a colorless oil.

Workup

  1. customThe mixture was then evaporated in vacuo
  2. customthe residual oil was purified on a silica gel flash chromatography column
  3. washeluted with 5% methanol/chloroform

Sources & evidence

ORD record
ord-b85dedc33cec438ba747476ab1a7e5c3
Source dataset
uspto-grants-1993_08
Patent number
US05240938

Reaction notes

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