Imidazole → 3-[(Tert-butyldimethylsilyl)oxy]phenol

HRID 2395924Notes

Reaction equation

HRID 2395924 reaction equation
[C:1]1([CH:8]=[CH:7][CH:6]=[C:4]([OH:5])[CH:3]=1)[OH:2].[Si:9](Cl)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10].N1C=CN=C1.C(OCC)(=O)C.CCCCCC>CN(C=O)C.O>[Si:9]([O:2][C:1]1[CH:3]=[C:4]([OH:5])[CH:6]=[CH:7][CH:8]=1)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 5054ResorcinolHCID 28928tert-Butyldimethylsilyl chlorideHCID 21226206Ethyl acetate hexane

Product 1

HCID 114474403-[(Tert-butyldimethylsilyl)oxy]phenolYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of resorcinol (1.0 g, 0.9 mmol) and tert-butyldimethylsilyl chloride (1.4 g, 0.9 mmol) in 5 mL of dry DMF was gradually added imidazole (1.2 g, 1.8 mmol) and the solution was stirred for 1 hour. TLC analysis (silica gel, 20% ethyl acetate/hexane) showed completion of reaction. The solution was poured into 25 mL of water and extracted with 3×25 mL of ether. The combined ether solutions were dried over anhydrous MgSO4. Evaporation of solvent gave an oil which was chromatographed on silica using 20% ethyl acetate/hexane to give the product as a white solid in 70% yield: 1H NMR (CDCl3) δ0.199 (s, 6H), 0.983 (s, 9H), 6.39-7.09 (m, 4H).

Workup

  1. customcompletion of reaction
  2. extractionextracted with 3×25 mL of ether
  3. dry with materialThe combined ether solutions were dried over anhydrous MgSO4
  4. customEvaporation of solvent
  5. customgave an oil which
  6. customwas chromatographed on silica using 20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-6f73acd66894408d92f6404b327fb017
Source dataset
uspto-grants-1996_02
Patent number
US05491072

Reaction notes

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