Sodium Hydroxide → HCID 66886312, compound

Participants

Reaction Steps

To a mixture of 7-hydroxy-1-(4-methylbenzyl)-1H-indole (1.36 g), acetobromo-α-D-glucose (2.59 g) and benzyltri-(n-butyl)ammonium chloride (1.79 g) in methylene chloride (20 mL) was added 5 mol/L aqueous sodium hydroxide solution (3.4 mL), and the mixture was stirred at room temperature overnight. The reaction mixture was purified by column chromatography on aminopropylated silica gel (eluent: n-hexane/ethyl acetate 1/1), and purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=3/1-2/1) to give 7-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1-(4-methylbenzyl)-1H-indole (1.25 g). The obtained 7-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-1-(4-methylbenzyl)-1H-indole (0.3 g) was dissolved in methanol (2 mL). To the solution was added sodium methoxide (28% methanol solution, 0.05 mL), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was purified by column chromatography on silica gel (eluent: methylene chloride/methanol=5/1) to give the title compound (0.19 g).

Provenance & Evidence