Imidazole → 6-((tert-butyldimethylsilyl)oxy)-1H-indole

HRID 1786690Notes

Reaction equation

HRID 1786690 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[Si:11](Cl)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].N1C=CN=C1.CN(C)C=O>C(OCC)(=O)C>[O:1]([C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1)[Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 5245086-Hydroxyindole

Product 1

HCID 222508166-((tert-butyldimethylsilyl)oxy)-1H-indoleYield 88.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5.5 g 6-hydroxyindole, 7.47 g tert-butyldimethylsilyl chloride, 7.03 g imidazole, and 25 mL dimethylformamide is stirred at ambient temperature for 20 h. The reaction is diluted with ethyl acetate, washed with water (2×), dried (MgSO4), and the solvent removed under reduced pressure to provide an oil. The oil is chromatographed, eluting with ethyl acetate/heptane, to afford 9.05 g (88%) of 6-(tert-butyldimethylsiloxy)-1H-indole as a white solid: TLC Rf 0.4 (silica, 1:9 ethyl acetate/heptane).

Workup

  1. washwashed with water (2×)
  2. dry with materialdried (MgSO4)
  3. customthe solvent removed under reduced pressure
  4. customto provide an oil
  5. customThe oil is chromatographed
  6. washeluting with ethyl acetate/heptane

Sources & evidence

ORD record
ord-9e5fc3ac1d3a4b60b4e53322e78f8a86
Source dataset
uspto-grants-2009_03
Patent number
US07507734B2

Reaction notes

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