反应详情

To 50 ml of methylene chloride were dissolved 0.9 g/4 mmol of 3,5-dimethyl-4-acetoxybenzoyl chloride and 0.5 g/1.9 mmol of 1,10-diaza-4,7,13,16-tetraoxacyclooctadecane, and to this solution was added 2.2 ml of triethylamine and a catalytic amount (40 mg/0.3 mmol) of diethylaminopyridine in an ice bath. The reaction mixture was refluxed under heat for 4 hours, and allowed to cool to room temperature. The reaction solution was washed with 1N hydrochloric acid, distilled water, saturated aqueous solution of sodium hydrogencarbonate, and saturated aqueous solution of sodium chloride, in this order. The organic layer was dried with anhydrous sodium sulfate, and after removing the drying agent, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography using methylene chloride-methanol for the eluting solution to obtain 1.1 g of the desired 1,10-bis(3',5'-dimethyl-4'-acetoxyphenylcarbonyl)-1,10-diaza-4,7,13,16-tetraoxacyclooctadecane. MS: 642 (M+), 451, 191. 1H-NMR (CDCl3): δ2.15 (6H, s), 2.34 (12H, s), 3.6 (16H, br), 3.8 (8H, br), 7.05 (4H, s).

1. temperatureThe reaction mixture was refluxed
2. temperatureunder heat for 4 hours
3. washThe reaction solution was washed with 1N hydrochloric acid
4. distillationdistilled water, saturated aqueous solution of sodium hydrogencarbonate, and saturated aqueous solution of sodium chloride
5. dry with materialThe organic layer was dried with anhydrous sodium sulfate
6. customafter removing the drying agent
7. customthe solvent was evaporated under reduced pressure
8. customThe residue was purified by silica gel column chromatography