反应详情

To a suspension of sodium hydride (50%; 0.6 g) (deprived of mineral oil) in tetrahydrofuran (10 ml), there was added dropwise a solution of 5-phenyl-4-pentenol [1.66 g; known compound; cf. e.g. Journal of the Chemical Society, page 1863 (1961)] in tetrahydruforan (10 ml) in argon atmosphere at room temperature. The mixture was stirred at the same temperature for 5 minutes. A solution of benzyl bromide (1.93 g) in tetrahydrofuran (10 ml) was added dropwise and the mixture was stirred at the same temperature for 20 hours. The tetrahydrofuran was distilled off under reduced pressure and water was added to the residue, followed by extraction with ether. After washing with water and drying over magnesium sulfate, the solvent was distilled off, and the residue was subjected to silica gel chromatography, elution being carried out with chlorofrom to give 5-benzyloxy-1-phenyl-1-pentene (2.5 g) as a colorless oil.

1. customat room temperature
2. stirringthe mixture was stirred at the same temperature for 20 hours
3. distillationThe tetrahydrofuran was distilled off under reduced pressure and water
4. additionwas added to the residue
5. extractionfollowed by extraction with ether
6. washAfter washing with water
7. dry with materialdrying over magnesium sulfate
8. distillationthe solvent was distilled off
9. washthe residue was subjected to silica gel chromatography, elution