Tetrabutylammonium Fluoride → N-Boc-5-Hydroxyindole

HRID 1359939Notes

Reaction equation

HRID 1359939 reaction equation
[Si]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:13]=[CH:12]2)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH:13]=[CH:12]2

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 23398221HCID 23398221, compound

Product 1

HCID 22596220N-Boc-5-Hydroxyindole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution (0.18 M) of tert-butyl 5-{[tert-butyl(dimethyl)silyl]oxy}-1H-indole-1-carboxylate in THF was treated with TBAF (1.1 eq) at 0° C. The mixture was stirred at that temperature for 10 min and allowed to reach room temperature. The reaction was quenched by the addition of saturated aqueous NH4Cl solution and extracted with ethyl acetate. The organic layer was washed with H2O, brine and dried over Na2SO4. The crude product was purified by column chromatography on silica gel (Petroleum ether:EtOAc 92/8) to afford the title compound as a colorless oil.

Workup

  1. customto reach room temperature
  2. customThe reaction was quenched by the addition of saturated aqueous NH4Cl solution
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with H2O, brine
  5. dry with materialdried over Na2SO4
  6. customThe crude product was purified by column chromatography on silica gel (Petroleum ether:EtOAc 92/8)

Sources & evidence

ORD record
ord-58aee2a7f5694d0ba50cfd67eb2d070b
Source dataset
uspto-grants-2011_02
Patent number
US07879815B2

Reaction notes

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