Tetrabutylammonium Fluoride → tert-Butyl (6-hydroxy-1H-indol-1-yl)acetate

HRID 915383Notes

Reaction equation

HRID 915383 reaction equation
[C:1]([O:5][C:6](=[O:25])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][Si](C(C)(C)C)(C)C)[CH:15]=2)[CH:10]=[CH:9]1)([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:1]([O:5][C:6](=[O:25])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:17])[CH:15]=2)[CH:10]=[CH:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 69279688[6-(Tert-butyl-dimethyl-silanyloxy)-indol-1-yl]-acetic acid tert-butyl ester

Product 1

HCID 69283069tert-Butyl (6-hydroxy-1H-indol-1-yl)acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To an ice cooled solution of [6-(tert-butyl-dimethyl-silanyloxy)-indol-1-yl]-acetic acid tert-butyl ester (4.2 g, 11.6 mmol) in THF (24 ml) was added a 1 M solution of tetrabutylammonium fluoride in THF (11.6 ml, 11.6 mmol) within 15 min. The reaction mixture was stirred for 1 h at ambient temperature, poured onto 1 N HCl/ice water 1/1 and extracted two times with ethyl acetate. The combined organic layers were washed with brine/ice water 1/1 and dried over sodium sulfate. The solvent was removed under reduced pressure to give 3.4 g (quant.) of the title compound as brown oil which was used in the next step without further purification.

Workup

  1. extractionextracted two times with ethyl acetate
  2. washThe combined organic layers were washed with brine/ice water 1/1
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-9a7e6afa06ff46548ad4348a1e90157e
Source dataset
uspto-grants-2007_09
Patent number
US07265149B2

Reaction notes

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