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

HRID 1767875Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1767875
[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]

Komponenten

5

Edukt 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

Produkt 1

HCID 69279689tert-Butyl (4-hydroxy-1H-indol-1-yl)acetateAusbeute 36,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-b67dbafbc8ab4933aa9b9c4c1147ebf9
Quelldatensatz
uspto-grants-2007_06
Patentnummer
US07235572B2

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