Cyclohexene → 1-Acetyl-5-carbomethoxy-7-chloro-4-methoxyindole

Participants

Reaction Steps

A 2.5% solution of osmium tetroxide in butanol (0.25 ml) is added to a stirred solution of the methoxy compound from step 7 above (1.5 g) in H2O-dioxane (15 ml/45 ml) and stirred for 30 minutes. Sodium periodate (2.25 g) is added portionwise over one hour and the reaction mixture stirred for 31/2 hours. Cyclohexene (1 ml) is added, the mixture stirred for one hour, diluted with H2O and extracted with CHCl3. The organic layer is separated, dried (MgSO4) and evaporated affording a gum which is dissolved in TFA and allowed to stand for 15 minutes. The acid solution is diluted to 100 mls with CH2Cl2 and washed with H2O, saturated NaHCO3, dried (MgSO4) and evaporated affording a solid which is chromatographed on silica gel affording a colorless solid which is the indole as confirmed by NMR (270 MHz, CDCl2).

Provenance & Evidence