反应详情

A solution of 6-(diethylaminocarbonyl)-2- naphthalenecarboxylic acid (18 g, 66 mmol) in THF (200 ml) was slowly added to a refluxing suspension of lithium aluminium hydride (7.5 g, 199 mmol) in THF (500 ml). The mixture was refluxed for an hour, then cooled at room temperature and treated with a mixture of THF (25 ml) and water (3.5 ml), with 20% sodium hydroxide (8.5 ml) and finally with water (33 ml). The white solid was filtered off and the solvent was removed under reduced pressure. Crude was dissolved in diethyl ether (200 ml) and extracted with 1N HCl (3×100 ml). The aqueous solution was treated with 32% sodium hydroxide and extracted with diethyl ether (3×100 ml). The organic solution was dried over anhydrous sodium sulphate and the solvent was removed under reduced pressure yielding 12.7 g (79% yield) of pure 6-(diethylaminomethyl)-2-naphthalenemethanol as thick oil.

1. temperatureThe mixture was refluxed for an hour
2. filtrationThe white solid was filtered off
3. customthe solvent was removed under reduced pressure
4. dissolutionCrude was dissolved in diethyl ether (200 ml)
5. extractionextracted with 1N HCl (3×100 ml)
6. additionThe aqueous solution was treated with 32% sodium hydroxide
7. extractionextracted with diethyl ether (3×100 ml)
8. dry with materialThe organic solution was dried over anhydrous sodium sulphate
9. customthe solvent was removed under reduced pressure