Imidazole → 4-(t-Butyldimethylsilyloxy)indole

HRID 2389366Notes

Reaction equation

HRID 2389366 reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([OH:10])[C:4]=2[CH:3]=[CH:2]1.[C:11]([Si:15]([CH3:18])([CH3:17])Cl)([CH3:14])([CH3:13])[CH3:12].N1C=CN=C1>CN(C=O)C>[Si:15]([O:10][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[CH:3]=[CH:2][NH:1]2)([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 754211H-indol-4-ol

Product 1

HCID 115939764-(t-Butyldimethylsilyloxy)indole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1H-indole-4-ol (2.4 g) in DMF (50 mL) was added tert-butyldimethylchlorosilane (2.7 g) and 1H-imidazole (1.5 g) at ambient temperature. The reaction mixture was stirred for 17 hours at ambient temperature. The resulting mixture was evaporated in vacuo and diluted with EtOAc. The organic layer was washed with water and brine and then dried over anhydrous MgSO4, filtered and evaporated in vacuo. The residue was purified by silicagel column chromatography (n-hexane:EtOAc=80:20-60:40) to give 4-{[tert-butyl(dimethyl)silyl]oxy}-1H-indole.

Workup

  1. customThe resulting mixture was evaporated in vacuo
  2. additiondiluted with EtOAc
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was purified by silicagel column chromatography (n-hexane:EtOAc=80:20-60:40)

Sources & evidence

ORD record
ord-7024745fd23a4ed6aaf425246ee8bc28
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

Loading…