Sodium Hydroxide → HCID 131718477, compound

Participants

Reaction Steps

3.45 g (0.0107 mol) of rac-cis-2,3,3a,4,5,9b-hexahydro-6-methoxy-3-(3-phenyl-propyl)-1H-benzo[e]indole were dissolved in 0.1211 of 48% aqueous HBr and boiled under reflux for 5 hours. The mixture was poured into an ice-cold aqueous solution of 42.8 g (1.07 mol) of NaOH. After the addition of solid NaHCO3 the mixture was extracted three times with CH2Cl2. The organic phase was washed with saturated aqueous NaHCO3 and NaCl solutions, dried with Na2SO4, filtered and concentrated. By chromatography over silica gel with cyclohexane/ethyl acetate 1:1 and crystallization in hexane/ethyl acetate there were obtained 2.53 g (77%) of rac-cis-2,3,3a,4,5,9b-hexahydro-3-(3-phenyl-propyl)-1H-benzo[e]indol-6-ol as whitish crystals with m.p. 98°-100°. The mother liquor was concentrated and the residue was chromatographed over silica gel with cyclohexane/ethyl acetate 1:1. There was obtained an additional 0.62 g of oily material (2.12 mmol, 19%); total yield: 96%.

Provenance & Evidence