反应详情

1-(4-Bromo-phenyl)-hex-5-en-1-ol (1 g) was dissolved in 0.5 M NaBH4 in diglyme (9 mL) and chilled in an ice bath. BF3.OEt2 (1 mL) in diglyme (4 mL) was added with vigorous stirring. Stirring was continued for 1 hour and water (1 mL) was added. 3M NaOH (2 mL) was added followed by 30% H2O2 (3 mL). Anhydrous K2CO3 (5 g) was added and the solvent was decanted. The K2CO3 was washed with ethyl acetate and the combined organics were dried (Na2SO4) and evaporated. Distillation under vacuum removed most of the remaining diglyme. The residue was purified by column chromatography (light petroleum:diethyl ether 2:1) to give a clear oil which solidified to give the title compound as a white powder. 13C NMR (CDCl3): δ 25.4, 25.6, 32.5, 39.0, 62.7, 73.8, 121.2, 127.7, 131.5 and 143.9. 1H NMR (CDCl3): δ 1.40 (4H, m), 1.52 (2H, m), 1.74 (2H, m), 3.61 (2H, t, J=6.5 Hz), 4.74 (1H, t, J=6.5 Hz), 7.20 (2H, d, J=8.2 Hz) and 7.41 (2H, d, J=8.2 Hz).

1. temperaturechilled in an ice bath
2. customthe solvent was decanted
3. washThe K2CO3 was washed with ethyl acetate
4. dry with materialthe combined organics were dried (Na2SO4)
5. customevaporated
6. distillationDistillation under vacuum
7. customremoved most of the remaining diglyme
8. customThe residue was purified by column chromatography (light petroleum:diethyl ether 2:1)
9. customto give a clear oil which