Tetrabutylammonium Fluoride → 5-(2-hydroxy-1-phenyl-ethyl)-1H-indole-2-carbonitrile

HRID 268901Notes

Reaction equation

HRID 268901 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(S([N:28]2[C:36]3[C:31](=[CH:32][C:33]([CH:37]([C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)[CH2:38][O:39][Si](C(C)(C)C)(C)C)=[CH:34][CH:35]=3)[CH:30]=[C:29]2[C:53]#[N:54])(=O)=O)C=CC=CC=1>>[OH:39][CH2:38][CH:37]([C:33]1[CH:32]=[C:31]2[C:36](=[CH:35][CH:34]=1)[NH:28][C:29]([C:53]#[N:54])=[CH:30]2)[C:47]1[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=1

Participants

3

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59831791benzenesulfonyl-5-[2-(tert-butyl-dimethyl-silanyloxy)-1-phenyl-ethyl]-1H-indole-2-carbonitrile

Product 1

HCID 598318545-(2-hydroxy-1-phenyl-ethyl)-1H-indole-2-carbonitrileYield 78.8%

Procedure

A solution of tetrabutylammonium fluoride (1.0 M in THF, 1.6 mL) was added to a solution of -benzenesulfonyl-5-[2-(tert-butyl-dimethyl-silanyloxy)-1-phenyl-ethyl]-1H-indole-2-carbonitrile (0.56 g, 1.055 mmol) and the resulting mixture was refluxed for several hours. The solvent was evaporated under reduced pressure and the residue was diluted with water and ethyl acetate. The organic layer was separated, washed with brine, dried over anhydrous sodium sulfate filtered and evaporated under reduced pressure. The crude residue was purified by flash chromatography (EtOAc/hexane, 35/65 to 50/50) to afford 218 mg (75% yield) of 5-(2-hydroxy-1-phenyl-ethyl)-1H-indole-2-carbonitrile CCLXX as a light yellow foam.

Workup

  1. temperaturethe resulting mixture was refluxed for several hours
  2. customThe solvent was evaporated under reduced pressure
  3. additionthe residue was diluted with water and ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customThe crude residue was purified by flash chromatography (EtOAc/hexane, 35/65 to 50/50)

Sources & evidence

ORD record
ord-72e2e1e65a9b418cacaec62d2b91ccca
Source dataset
uspto-grants-2008_11
Patent number
US07446118B2

Reaction notes

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