Hydroquinone → 4-(tert-Butyldimethylsiloxy)phenol

HRID 2075628Notes

Reaction equation

HRID 2075628 reaction equation
[C:1]1([CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)[OH:2].N1C=CN=C1.[Si:14](Cl)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]>CN(C=O)C>[Si:14]([O:2][C:1]1[CH:8]=[CH:7][C:5]([OH:6])=[CH:4][CH:3]=1)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 785Hydroquinone2×HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 5973884-(tert-Butyldimethylsiloxy)phenolYield 53.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To an ice-cooled solution of hydroquinone (Compound 17; 3.3 g, 30 mmol) in DMF (60 ml), a solution of imidazole (3.1 g, 45 mmol) and tert-butyldimethylsilyl chloride (4.5 g, 30 mmol) in DMF (30 ml) was added; the ice bath was removed, and this was followed by overnight stirring at room temperature. This was poured over water to stop the reaction, after which extraction from ether was conducted. The combined organic phases were washed with saturated brine, thereafter dried with sodium sulfate. After filtration and concentration under reduced pressure, the residue obtained was purified by silica gel column chromatography [Biotage, eluent (9:1 n-hexane:ethyl acetate)] to yield Compound 18 (white solid 3.6 g, 53%).

Workup

  1. customthe ice bath was removed
  2. additionThis was poured over water
  3. customthe reaction
  4. extractionafter which extraction from ether
  5. washThe combined organic phases were washed with saturated brine
  6. dry with materialdried with sodium sulfate
  7. filtrationAfter filtration and concentration under reduced pressure
  8. customthe residue obtained
  9. customwas purified by silica gel column chromatography [Biotage, eluent (9:1 n-hexane:ethyl acetate)]

Sources & evidence

ORD record
ord-e79d13fa59b047aaa5cb2bc4a33670e2
Source dataset
uspto-grants-2011_04
Patent number
US07919653B2

Reaction notes

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