Diethyl Ether → tert-Butyl (4-hydroxy-1H-indol-1-yl)acetate

HRID 1767875Notes

Reaction equation

HRID 1767875 reaction equation
[C:1]([O:5][C:6](=[O:25])[CH2:7][N:8]1[C:16]2[C:11](=[C:12]([O:17][Si](C(C)(C)C)(C)C)[CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)([CH3:4])([CH3:3])[CH3:2].O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)C>C1COCC1>[C:1]([O:5][C:6](=[O:25])[CH2:7][N:8]1[C:16]2[C:11](=[C:12]([OH:17])[CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 162116731-Butanaminium, N,N,N-tributyl-, fluoride, hydrateHCID 69283774[4-(Tert-butyl-dimethyl-silanyloxy)-indol-1-yl]-acetic acid tert-butyl ester

Product 1

HCID 69279689tert-Butyl (4-hydroxy-1H-indol-1-yl)acetateYield 36.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To an ice cooled solution of 198 mg (0.55 mmol) [4-(tert-butyl-dimethyl-silanyloxy)-indol-1-yl]-acetic acid tert-butyl ester in 2 ml of THF was added a 1 M solution of tetrabutylammonium fluoride hydrate in tetrahydrofuran (0.55 ml, 0.55 mmol). The reaction mixture was stirred for 1 h at ambient temperature. Diethyl ether was added and the ether solution was washed with saturated aqueous NH4Cl solution, water and brine. Evaporation of the solvent under reduced pressure gave 49 mg (0.2 mmol, 36%) of (4-hydroxy-indol-1-yl)-acetic acid tert-butyl ester as white crystals.

Workup

  1. washthe ether solution was washed with saturated aqueous NH4Cl solution, water and brine
  2. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-b67dbafbc8ab4933aa9b9c4c1147ebf9
Source dataset
uspto-grants-2007_06
Patent number
US07235572B2

Reaction notes

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