Triethylamine → HCID 9828351, compound

Participants

Reaction Steps

The 5-O-(4-chlorobenzoyl)-3-C-ethynyl-D-ribofuranose (1.0 g; 3.20 mmol) obtained in Example 6 was suspended in dichloromethane (12 ml). To the resultant suspension were added 4-dimethylaminopyridine (12 mg; 0.098 mmol) and triethylamine (1.56 ml; 11.2 mmol). The mixture was cooled on ice. Ethyl chlorocarbonate (1.07 ml; 11.2 mmol) was added thereto and the liquid temperature was returned to room temperature. The mixture was stirred for one hour. The solvent was evaporated under reduced pressure. Ethyl acetate (40 ml) and water (40 ml) were added to the residue, then phases were separated. The ethyl acetate phase was washed once with saturated aqueous sodium hydrogencarbonate solution, then dried over magnesium sulfate. After filtration, the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:3), yielding 1.42 g (yield: 84.0%) of the title compound as a colorless oily substance.

Provenance & Evidence