Selenium Dioxide → 4-formyl-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester

Participants

Reaction Steps

A mixture of 1.6 g of 6-(2-methoxyphenyl)-2,2,4-trimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester, 20 mL of 1,4-dioxane, and 1.4 g of selenium dioxide was refluxed for half an hour. Another 1.4 g portion of selenium dioxide was added. The reaction was allowed to reflux for 6 hours. The reaction mixture was then filtered through diatomaceous earth and the residue was rinsed with EtOAc. The solvent was evaporated in vacuo and the residue was purified by flash chromatography to yield 1 g of 4-formyl-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester as a solid.

Provenance & Evidence