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

HRID 915383Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 915383
[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]

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-9a7e6afa06ff46548ad4348a1e90157e
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07265149B2

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