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

HRID 751197

Reaction equation

HRID 751197 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.C(OCC)C>[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 68822475HCID 68822475, compound

Product 1

HCID 57675474(5-Hydroxy-indol-1-yl)-acetic acid ethyl esterYield 83.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To an ice cold solution of [5-(tert-butyl-dimethyl-silanyloxy)-indol-1-yl]-acetic acid ethyl ester (12.9 g, 38.7 mmol) in THF (130 ml) was added tetrabutylammonium fluoride hydrate (12.5 g, 38.7 mmol). The reaction mixture was stirred for 1 h at RT, diluted with diethyl ether and washed with 1N HCl and water. Evaporation of the solvent under reduced pressure gave 7.07 g (32.2 mmol, 83%) (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-aeb47a2804d746b88049c024f3a62655
Source dataset
uspto-grants-2008_07
Patent number
US07405236B2

Linked notes

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