反应详情

To a solution of 1-(benzyloxy)-2-naphthaldehyde (7.00 g, 26.7 mmol) in methanol (250 mL) at 0° C. was added sodium borohydride (1.51 g, 40.0 mmol) and the reaction mixture was allowed to stir at room temperature for 24 h. The solvent was removed in vacuo to give a crude solid which was partitioned between ethyl acetate (300 mL) and water (300 mL). The organic layer was separated and washed with water (300 mL), aqueous sodium chloride (300 mL), dried (magnesium sulfate) and filtered through a plug of silica (10 cm×5 cm). The solvent was removed in vacuo to give 6.98 g (99%) of [1-(benzyloxy)-2-naphthyl]methanol as white crystalline solid. Rf=0.36 (silica, dichloromethane:hexanes 3:2); mp 85-87° C. Anal. Calcd. for C18H16O2: C, 81.24; H, 6.14. Found: C, 81.03; H, 5.98.

1. customThe solvent was removed in vacuo
2. customto give a crude solid which
3. customwas partitioned between ethyl acetate (300 mL) and water (300 mL)
4. customThe organic layer was separated
5. washwashed with water (300 mL), aqueous sodium chloride (300 mL)
6. dry with materialdried (magnesium sulfate)
7. filtrationfiltered through a plug of silica (10 cm×5 cm)
8. customThe solvent was removed in vacuo