1-Butanaminium, N,N,N-tributyl-, fluoride, hydrate → (5-Hydroxy-indol-1-yl)-acetic acid ethyl ester

HRID 890419Notes

Reaction equation

HRID 890419 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([O:15][Si](C(C)(C)C)(C)C)=[CH:12][CH:13]=2)[CH:8]=[CH:7]1)[CH3:2].O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.CCOCC>[CH2:1]([O:3][C:4](=[O:23])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([OH:15])=[CH:12][CH:13]=2)[CH:8]=[CH:7]1)[CH3:2]

Participants

5

Reactant 2

HCID 162116731-Butanaminium, N,N,N-tributyl-, fluoride, hydrateHCID 68822475[5-(Tert-butyl-dimethyl-silanyloxy)-indol-1-yl]-acetic acid ethyl ester

Product 1

HCID 57675474(5-Hydroxy-indol-1-yl)-acetic acid ethyl esterYield 83.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To an ice cooled solution of 12.9 g (38.7 mmol) [5-(tert-butyl-dimethyl-silanyloxy)-indol-1-yl]-acetic acid ethyl ester in 130 ml of THF was added 12.45 g (38.7 mmol) of tetrabutylammonium fluoride hydrate. The reaction mixture was stirred for 1 h at RT, taken up in ether and washed with 1N HCl and water. Evaporation of the solvent under reduced pressure gave 7.07 g (83%) of pure (5-hydroxy-indol-1-yl)-acetic acid ethyl ester.

Workup

  1. washwashed with 1N HCl and water
  2. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-a9568a99e6b84be3bc0ee3519441c060
Source dataset
uspto-grants-2006_02
Patent number
US06995263B2

Reaction notes

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