Imidazole → 4-(t-Butyldimethylsilyloxy)indole

HRID 1351987Notes

Reaction equation

HRID 1351987 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.N1C=CN=C1.[C:16]([Si:20](Cl)([CH3:22])[CH3:21])([CH3:19])([CH3:18])[CH3:17]>C(Cl)(Cl)Cl>[Si:20]([O:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:22])[CH3:21]

Participants

5

Reactant 3

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

Product 1

HCID 115939764-(t-Butyldimethylsilyloxy)indoleYield 37.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a suspension of 4-hydroxyindole (5.65 g, 42.4 mmol) in chloroform (200 mL) are added imidazole (4.33 g, 63.6 mmol) and tert-butylchlorodimethylsilane (7.03 g, 46.6 mmol), and the mixture is stirred at room temperature for 2.5 hours. The reaction mixture is washed with a mixture of a saturated brine and water (1:1, 100 mL), and the organic layer is dried over anhydrous potassium carbonate, filtered, and the filtrate is concentrated to about 50 mL under reduced pressure. The resultant is purified by silica gel column (300 g, ethyl acetate:hexane=1:5→1:1) to give the title compound as a white solid (3.90 g, yield: 37%), and the starting compound (2.62g, recovery rate: 46%).

Workup

  1. washThe reaction mixture is washed with a mixture of a saturated brine and water (1:1, 100 mL)
  2. dry with materialthe organic layer is dried over anhydrous potassium carbonate
  3. filtrationfiltered
  4. concentrationthe filtrate is concentrated to about 50 mL under reduced pressure
  5. customThe resultant is purified by silica gel column (300 g, ethyl acetate:hexane=1:5→1:1)

Sources & evidence

ORD record
ord-77b5a6d210934f89a1908511556f161b
Source dataset
uspto-grants-2007_05
Patent number
US07217724B2

Reaction notes

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