Diethyl Ether → Phenol, 4-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-

HRID 1987830Notes

Reaction equation

HRID 1987830 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][O:34][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36])=[CH:29][CH:28]=1)(C(C)(C)C)(C)C.[NH4+].[Cl-].CCOCC>C1COCC1>[Si:35]([O:34][CH2:33][C:30]1[CH:31]=[CH:32][C:27]([OH:26])=[CH:28][CH:29]=1)([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 108935701-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-4-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]benzene

Product 1

HCID 11230163Phenol, 4-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-Yield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutylammonium fluoride (1 M THF, 44 mL, 44 mmol) was added to a 0° C. solution of 1-(tert-butyldimethylsilyloxy)-4-((tert-butyldimethylsilyloxy)methyl)benzene (14 g, 40 mmol) in THF (400 mL). The reaction was stirred for 30 minutes, then poured into a mixture of saturated NH4Cl and Et2O. The layers were separated and the aqueous phase was extracted twice with Et2O. The organics were combined, washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was chromatographed (1:9 EtOAc/hexanes) to provide the product as a colorless oil (8.0 g, 85%).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous phase was extracted twice with Et2O
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was chromatographed (1:9 EtOAc/hexanes)

Sources & evidence

ORD record
ord-ba6191afb576451498c86c9e182ba568
Source dataset
uspto-grants-2009_06
Patent number
US07553842B2

Reaction notes

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