Tetrabutylammonium Fluoride → HCID 57443572, compound

HRID 547133Notes

Reaction equation

HRID 547133 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C([Si](C)(C)[O:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]([OH:36])([CH2:34][CH3:35])[CH2:32][CH3:33])=[CH:27][C:26]=1[O:37][CH3:38])(C)(C)C>O1CCCC1.C(OCC)(=O)C>[CH2:32]([C:31]([C:28]1[CH:29]=[CH:30][C:25]([OH:24])=[C:26]([O:37][CH3:38])[CH:27]=1)([OH:36])[CH2:34][CH3:35])[CH3:33]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 57709088HCID 57709088, compound

Product 1

HCID 57443572HCID 57443572, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A 1 M solution of tetrabutylammonium fluoride in tetrahydrofuran (24.7 mL, 24.7 mmol) was added to a solution of 3-[4-(t-butyl-dimethyl-silanyloxy)-3-methoxy-phenyl]-pentan-3-ol (Example 176-(2); 8.0 g, 24.7 mmol) in tetrahydrofuran (30 mL) at room temperature, and the mixture was stirred at room temperature for 30 minutes. The reaction solution was diluted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium bicarbonate solution and water, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane only to hexane:ethyl acetate=1:1) to give the title compound (4.25 g, 83%).

Workup

  1. washThe organic layer was washed with a saturated aqueous sodium bicarbonate solution and water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel chromatography (hexane only to hexane

Sources & evidence

ORD record
ord-4d38faffddcf4a58aaf17c2ff41f5ee9
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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