Imidazole → 4-(t-Butyldimethylsilyloxy)indole

HRID 51468Notes

Reaction equation

HRID 51468 reaction equation
N1C=CN=C1.[OH:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH:9]=[CH:10][NH:11]2.[Si:16](Cl)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17].O>C(Cl)Cl>[C:19]([Si:16]([CH3:18])([CH3:17])[O:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH:9]=[CH:10][NH:11]2)([CH3:22])([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 754211H-indol-4-ol

Product 1

HCID 115939764-(t-Butyldimethylsilyloxy)indole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Imidazole (15.3 g, 225 mmol) was added to a solution of 4-hydroxyindole (20 g, 150 mmol) in 300 mL of anhydrous methylene chloride at ambient temperature. The resulting mixture was treated with tert-butyldimethylsilyl chloride (25 g, 165 mmol). After stirring overnight at ambient temperature, the reaction mixture was poured into 300 mL of water. The layers were separated, and the aqueous phase was extracted with methylene (2×100 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to a black oil. The crude residue was purified on a Prep 500 (silica gel; 0% to 5% ethyl acetate/hexanes) to give the title compound as a light purple waxy solid in quantitative yield. MS (ion spray, NH4OAc) m/e [M+1]+ 248, [M−1]− 246.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous phase was extracted with methylene (2×100 mL)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo to a black oil
  6. customThe crude residue was purified on a Prep 500 (silica gel; 0% to 5% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-c200170422d64c2696370ce4df865310
Source dataset
uspto-grants-2004_03
Patent number
US06713645B1

Reaction notes

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