Methanol → HCID 19995020, compound

Participants

Reaction Steps

para-Toluenesulfonic acid hydrate (0.55 g) was added to a stirred solution of methyl 4-[5-(2-methoxyvinyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoate (0.2 g) in 1:1 methanol:methylene chloride (5 ml), under a nitrogen atmosphere. After 4 h, the mixture was evaporated at ambient temperature, and the product was purified by flash chromatography, eluting with 4:1 hexane:ethyl acetate, to give methyl 4-[5-(2,2-dimethoxyethyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoate (0.19 g, 88%) as an oil; partial NMR (300 MHz, DMSO-d6): 0.81(t, 3H, CH3), 1.71(m, 2H, CH2), 2.84(m, 2H, CH2), 3.20(s, 6H, 2xOCH3), 3.83(s, 3H, OCH3), 3.91(s, 3H, OCH3), 4.02(m, 4H, NCH2, ArCH2Ar'), 4.50(t, 1H, CH).

Provenance & Evidence