反应详情

温度

5 °C

Dissolve (2,6-Dimethoxy-naphthalen-1-yl)-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone in CH2Cl2 (10 volume equivalents) in a 3-neck round bottom flask equipped with a pressure equalizing addition funnel, stirbar, and N2 source. Cool the flask in an ice/brine bath and add 1.0 M BCl3 solution in CH2Cl2 (1.2 equivalents) dropwise. The reaction solution turns dark red and the temperature initially increases to 5° C. Within one hour, all starting material is consumed, as determined by TLC (1:1, Ether:Petroleum Ether). Quench the reaction with methanol (5 equivalents) and allow to warm to room temperature. Dilute the organic solution with CH2Cl2 (one volume equivalent) and add to a 1.0 M NaHCO3 solution (5 volume equivalents) and stir for one hour. Separate the aqueous and organic layers. Wash the aqueous layer with CH2Cl2 (one volume) and the combine organic layers, wash with saturated NH4Cl and dry over Na2SO4. Purify the product via column chromatography (50/1 silica gel) eluting with CH2Cl2/Hexanes (3/1) to yield (2-hydroxy-6-methoxy-naphthalen-1-yl)-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone (typical yield 87%).

1. customequipped with a pressure
2. additionaddition funnel
3. temperatureCool the flask in an ice/brine bath
4. customall starting material is consumed
5. customQuench
6. temperatureto warm to room temperature
7. customSeparate the aqueous and organic layers
8. washWash the aqueous layer with CH2Cl2 (one volume)
9. washthe combine organic layers, wash with saturated NH4Cl
10. dry with materialdry over Na2SO4
11. customPurify the product via column chromatography (50/1 silica gel)
12. washeluting with CH2Cl2/Hexanes (3/1)