Tetrabutylammonium Fluoride → Tert-butyl 3-{4-[(4'-hydroxy-2',6'-dimethylbiphenyl-3-yl)methoxy]phenyl}propanoate

HRID 273404Notes

Reaction equation

HRID 273404 reaction equation
[Si]([O:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][O:23][C:24]3[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[CH:26][CH:25]=3)[CH:17]=2)=[C:11]([CH3:39])[CH:10]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[OH:8][C:9]1[CH:10]=[C:11]([CH3:39])[C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][O:23][C:24]3[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][C:32]([O:34][C:35]([CH3:37])([CH3:36])[CH3:38])=[O:33])=[CH:26][CH:25]=3)[CH:17]=2)=[C:13]([CH3:15])[CH:14]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 58903174HCID 58903174, compound

Product 1

HCID 58903199Tert-butyl 3-{4-[(4'-hydroxy-2',6'-dimethylbiphenyl-3-yl)methoxy]phenyl}propanoateYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 3-{4-[(4′-{[tert-butyl(dimethyl)silyl]oxy}-2′,6′-dimethylbiphenyl-3-yl)methoxy]phenyl}propanoate (2.38 g, 4.35 mmol) in tetrahydrofuran (24 mL) was added tetrabutylammonium fluoride (1 M tetrahydrofuran solution, 4.79 mmol, 4.79 mL) at room temperature with stirring and the mixture was stirred at room temperature for 2 hrs. The reaction mixture was concentrated under reduced pressure and the residue was partitioned between water and ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=3/1) to give the title compound (1.69 g, yield 90%) as a colorless oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hrs
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was partitioned between water and ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-165d3208b6ae46eeb80fa7595e972600
Source dataset
uspto-grants-2008_11
Patent number
US07456218B2

Reaction notes

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