反应详情

To 3-hydroxy-6,7-dimethoxyquinoline (150 mg; 0.73 mmol) in 3 mL THF is added benzyl bromide (0.13 mL; 188 mg; 1.10 mmol) and NaH (59 mg; 1.46 mmol). This is stirred at room temperature for 1 hour and 25 mg of NaH added followed by 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)pyrimidinone (DMPU) (255 mg; 2.07 mmol) and stirred at room temperature for 31/2 hours. The reaction mixture is partitioned between EtOAc and distilled H2O and extracted 2× with EtOAc. The latter is washed with brine, dried (MgSO4), filtered, evaporated to dryness and chromatographed with 1% MeOH/CHCl3 to obtain 3-benzyloxy-6,7-dimethoxyquinoline m.p. 146.5°-148.5° C.).

1. stirringstirred at room temperature for 31/2 hours
2. customThe reaction mixture is partitioned between EtOAc
3. distillationdistilled H2O
4. extractionextracted 2× with EtOAc
5. washThe latter is washed with brine
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. customevaporated to dryness
9. customchromatographed with 1% MeOH/CHCl3