Imidazole → 5-(tert-Butyldimethylsilyloxy)-1H-indole

HRID 1767958Notes

Reaction equation

HRID 1767958 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[Si:11](Cl)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].N1C=CN=C1>CN(C=O)C.CCOCC>[C:14]([Si:11]([CH3:13])([CH3:12])[O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2)([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 160545-HydroxyindoleHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 222508175-(tert-Butyldimethylsilyloxy)-1H-indoleYield 100%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A suspension of 5-hydroxy-indol (5 g, 38 mmol), tert-butyldimethylsilyl chloride (6.1 g, 39.4 mmol) and imidazole (5.4 g, 68 mmol) in DMF (50 ml) was stirred for 20 h at RT. The reaction mixture was taken up in ether and washed with 1N HCl and water. The organic layer was dried over sodium sulfate and concentrated under reduced pressure to give 9.4 g (38 mmol, quant.) 5-(tert-butyl-dimethyl-silanyloxy)-1H-indole.

Workup

  1. washwashed with 1N HCl and water
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0239daa7befe4aee80832a33a78985d1
Source dataset
uspto-grants-2007_06
Patent number
US07235572B2

Reaction notes

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