Dimethyl Sulfoxide → 2-(3-Pyridylcarbonyl)-6-(2-methyl-1,3-dioxolan-2-yl)naphthalene

Participants

Reaction Steps

A solution of 165 mg of oxalyl chloride in 20 ml of methylene chloride was cooled to -50° C., 203 mg of dimethylsulfoxide added dropwise, and the mixture stirred for 5 minutes. A solution of 321 mg of 2-[(3-pyridyl)hydroxymethyl]-6-(2-methyl-1,3-dioxolan-2-yl)naphthalene in 10 ml of methylene chloride was then added dropwise and the mixture stirred at -50° C. for 15 minutes. Triethylamine (506 mg) was added at -50° C. and the mixture stirred for 5 minutes, then allowed to warm to room temperature. The solution was washed with water, dried over sodium sulfate and the solvent removed under reduced pressure to give 300 mg of 2-(3-pyridylcarbonyl)-6-(2-methyl-1,3-dioxolan-2-yl)naphthalene as an oil.

Provenance & Evidence