1-Butanaminium, N,N,N-tributyl-, fluoride, hydrate → 3-ethyl-1H-indol-5-ol

HRID 1767961Notes

Reaction equation

HRID 1767961 reaction equation
O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C([Si](C)(C)[N:25]1[C:33]2[C:28](=[CH:29][C:30]([O:34][Si](C(C)(C)C)(C)C)=[CH:31][CH:32]=2)[C:27]([CH2:42][CH3:43])=[CH:26]1)(C)(C)C>C1COCC1.C(OCC)(=O)C>[CH2:42]([C:27]1[C:28]2[C:33](=[CH:32][CH:31]=[C:30]([OH:34])[CH:29]=2)[NH:25][CH:26]=1)[CH3:43]

Participants

5

Reactant 2

HCID 162116731-Butanaminium, N,N,N-tributyl-, fluoride, hydrateHCID 236144791-(tert-butyl-dimethyl-silanyl)-5-(tert-butyl-dimethyl-silanyloxy)-3-ethyl-1H-indole

Product 1

HCID 153663373-ethyl-1H-indol-5-olYield 74%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Tetrabutylammonium fluoride hydrate (1.4 g, 4.3 mmol) was added to an ice-cooled solution of 1-(tert-butyl-dimethyl-silanyl)-5-(tert-butyl-dimethyl-silanyloxy)-3-ethyl-1H-indole (840 mg, 2.2 mmol) in THF (8 ml). The reaction mixture was stirred for 45 min at ambient temperature, diluted with ethyl acetate and washed with 1 N HCl and water. The organic phase was concentrated under reduced pressure and the crude product purified by column chromatography (silica gel, ethyl acetate/heptane 1:2) to give 258 mg (1.6 mmol, 74%) 3-ethyl-1H-indol-5-ol.

Workup

  1. washwashed with 1 N HCl and water
  2. concentrationThe organic phase was concentrated under reduced pressure
  3. customthe crude product purified by column chromatography (silica gel, ethyl acetate/heptane 1:2)

Sources & evidence

ORD record
ord-c8a61614552e4894a270f8952fa249b1
Source dataset
uspto-grants-2007_06
Patent number
US07235572B2

Reaction notes

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