Triethylamine → HCID 67490982, compound

Participants

Reaction Steps

A solution of a sulfur trioxide-pyridine complex (23.7 g, 149 mmol) in dimethyl sulfoxide (150 mL) was added to a solution of 2-(tritylamino)methyl-3,4,5,6-tetrahydro-2H-pyran-3-ol (18.54 g, 49.6 mmol) and triethylamine (45 mL, 323 mmol) in dimethyl sulfoxide (150 mL) in a nitrogen atmosphere at room temperature. The mixture was stirred at the same temperature for 10 hours. The reaction solution was poured into ice water (1 L), followed by extraction with ethyl acetate (2×1 L). Then, the organic layers were combined and washed with water (2×1 L) and brine (1 L). The resulting organic layer was dried over anhydrous sodium sulfate and filtered. Then, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=5:95→10:90→20:80) to give 9.56 g (52%) of the title compound as a colorless transparent gummy solid.

Provenance & Evidence