4-Nitrobenzaldehyde → HCID 11858516, compound

Participants

Reaction Steps

1-Phenylpent-3-yn-1-ol (50 mg, 0.31 mmol) and 4-nitrobenzaldehyde (0.057 mg, 0.37 mmol) were dissolved in methylene chloride (3.0 mL). After the temperature was lowered to −78° C., trimethylsilyl trifluoromethanesulfonate (TMSOTf) (170 mL, 0.93 mmol) was added, and the solution was stirred for one hour at the same temperature. The temperature was slowly elevated to room temperature for about 3 hours, and the solution was further stirred for another one hour at room temperature. The solution was added with an aqueous NaHCO3 solution and diluted with diethylether. The organic layer was washed with water and brine, dried with MgSO4, filtered and condensed. A pure target compound (31 mg) was obtained with a yield of 77% by using column chromatography.

Provenance & Evidence