tert-Butanol → HCID 53784393, Verbindung

Reaktionsgleichung

[C:1]([OH:5])(C)([CH3:3])[CH3:2].[CH2:6]([C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]([CH3:19])[CH:11]=1)CC=C.S([O-])([O-])=[O:21].[Na+].[Na+]>O>[CH3:19][N:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]([CH2:6][CH2:2][C@H:1]([OH:5])[CH2:3][OH:21])=[CH:11]1

Komponenten

Versuchsvorschrift

To a mixture of tert-butyl alcohol (14 ml) and water (14 ml) was added AD-mix-a (4.0 g). The mixture was stirred at room temperature until both phases are clear, and then cooled to 0° C. 3-(3-butenyl)-1-methylindole (530 mg, 2.86 mmol) was added, and the heterogeneous slurry was stirred vigorously at 0° C. for 4 hours. While the mixture was stirred at 0° C., solid sodium sulfite (4.29 g) was added and the mixture was allowed to warm to room temperature and stirred for 1 hour. This mixture was extracted with ethyl acetate, and the extracts were washed with brine, dried (magnesium sulfate) and evaporated in vacuo. The residue was purified by silica gel (15 g) chromatography eluting with chloroform/methanol (100:1 to 20:1) to give (S)-4-(1-methylindol-3-yl)butane-1,2-diol (602 mg, 96.1%).