반응 #667834

반응 방정식

2-(chloromethyl)quinoline

NaH

7-hydroxy-1-tetralone

→

yellow crystals

수율 35.0%

3,4-Dihydro-7-(2-quinolinylmethoxy)-1(2H)-naphthalenone

수율 35.0%

용매

dimethylformamide

dimethylformamide

반응 조건

후처리

1. 1
   workup.WAITAfter half an hour
2. 2
   기타The ice bath is removed
3. 3
   기타The solvent is then removed in vacuo
4. 4
   기타the residue is partitioned between 1N sodium hydroxide and methylene chloride
5. 5
   기타The organic layer is separated
6. 6
   건조dried over magnesium sulfate
7. 7
   기타evaporated down to an oil
8. 8
   기타chromatographed on silica gel
9. 9
   세척Elution with 9-1 methylene chloride/ethyl acetate
10. 10
    기타gives 2.0 g (54%)
11. 11
    기타This material is recrystallized from acetonitrile

실험 절차

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.

출처