Tetrabutylammonium Fluoride → 6-(4-hydroxy-cyclohex-1-enyl)-1-methyl-1H-indole-3-carboxylic acid methyl ester
Reaktionsgleichung
[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH2:19][CH2:18][CH:17]([O:20][Si](C(C)(C)C)(C)C)[CH2:16][CH:15]=3)=[CH:11][CH:12]=2)[N:7]([CH3:28])[CH:6]=1)=[O:4].[N+](CCCC)(CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH2:19][CH2:18][CH:17]([OH:20])[CH2:16][CH:15]=3)=[CH:11][CH:12]=2)[N:7]([CH3:28])[CH:6]=1)=[O:4]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A solution of 6-[4-(tert-butyl-dimethyl-silanyloxy)-cyclohex-1-enyl]-1-methyl-1H-indole-3-carboxylic acid methyl ester (0.710 g, 1.78 mmol) in THF (10 mL) is treated with Bu4NF (2.22 mL, 1.0 M in THF). The mixture is stirred at room temperature for 5 h and concentrated under reduced pressure. The residue is purified by silica gel chromatography eluting with a gradient of 25-80% EtOAc/Hexanes to provide the 6-(4-hydroxy-cyclohex-1-enyl)-1-methyl-1H-indole-3-carboxylic acid methyl ester (0.320 g, 63%). MS m/z 286.3 (M+1).