反应详情

To a slurry of NaH (0.29 g, 12.25 mmol) in 25 mL dimethylformamide under nitrogen at 0° C. is added portionwise 7-hydroxy-1-tetralone (2.0 g, 12.33 mmol) over 5 minutes. After half an hour, 2-(chloromethyl)quinoline (2.2 g, 12.43 mmol) is added in 10 mL dimethylformamide. The ice bath is removed and the reaction mixture is stirred overnight. The solvent is then removed in vacuo and the residue is partitioned between 1N sodium hydroxide and methylene chloride. The organic layer is separated, dried over magnesium sulfate, evaporated down to an oil, and chromatographed on silica gel. Elution with 9-1 methylene chloride/ethyl acetate gives 2.0 g (54%). This material is recrystallized from acetonitrile to afford 1.3 g (35%) of yellow crystals, m.p. 98.5°-101.5° C.

1. waitAfter half an hour
2. customThe ice bath is removed
3. customThe solvent is then removed in vacuo
4. customthe residue is partitioned between 1N sodium hydroxide and methylene chloride
5. customThe organic layer is separated
6. dry with materialdried over magnesium sulfate
7. customevaporated down to an oil
8. customchromatographed on silica gel
9. washElution with 9-1 methylene chloride/ethyl acetate
10. customgives 2.0 g (54%)
11. customThis material is recrystallized from acetonitrile