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

HRID 890417Notes

Reaction equation

HRID 890417 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 101.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 5 g (37.55 mmol) of 5-hydroxy-indole, 6.13 g (39.4 mmol) of tert-butyldimethylsilyl chloride and 5.37 g (68.1 mmol) of imidazole in 50 ml DMF was stirred for 20 h at RT. The reaction mixture was taken up in ether, washed with 1N HCl and water and the ether solution was then concentrated under reduced pressure, to give 9.4 g (quant.) of clean 5-(tert-butyl-dimethyl-silanyloxy)-1H-indole.

Workup

  1. washwashed with 1N HCl and water
  2. concentrationthe ether solution was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-26772690d74448f38db225fe789374bb
Source dataset
uspto-grants-2006_02
Patent number
US06995263B2

Reaction notes

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