反应详情

To a mixture of water (0.8 ml) and tert-butyl alcohol (3 ml) were added methyl 6-formyl-3-methylquinoline-2-carboxylate (140 mg) , 2-methyl-2-butene (190 mg) and sodium dihydrogenphosphate (105 mg) in water bath. To the mixture was added dropwise sodium chloride (244 mg) and the mixture was stirred for 1 hour at the same temperature. The reaction mixture was cooled in an ice bath, adjusted to pH 4 with 1M hydrochloric acid and extracted with dichloromethane. The organic layer was dried over magnesium sulfate and evaporated in vacuo. The residue was purified by preparative thin-layer chromatography (dichloromethane:methanol=10:1, V/V) followed by crystallization from methanol-isopropyl ether to give 2-methoxycarbonyl-3-methylquinoline-6-carboxylic acid (121 mg) as crystals.

1. temperatureThe reaction mixture was cooled in an ice bath
2. extractionextracted with dichloromethane
3. dry with materialThe organic layer was dried over magnesium sulfate
4. customevaporated in vacuo
5. customThe residue was purified by preparative thin-layer chromatography (dichloromethane:methanol=10:1, V/V)
6. customfollowed by crystallization from methanol-isopropyl ether