反应详情

温度

0 °C

Place lithium hexamethyldisilazane (2 mL of a 1M solution in tetrahydrofuran, 2 mmol) and tetrahydrofuran (8 mL) under an argon atmosphere and cool to 0° C. Add a solution of 3-(4methoxybenzyloxy)phenylacetylene (0.48 g, 2 mmol) in tetrahydrofuran and stir the brown solution for 45 minutes at 0° C. Add N-methoxy-N-methylbenzamide (0.4 g, 2.4 mmol), remove the cooling bath andstir at room temperature for 1 hour. Partition the mixture between ethyl ether and water, separate the organic phase and dry (MgSO4). Filter and evaporate the solvent in vacuo to yield an oil. Filter through silica gel and elute with 10% ethyl acetate/hexane to yield a crude solid. Recrystallize (hexane, ethyl ether) to yield 0.26 g (lst crop) and 0.15 g (2nd crop) of the title compound; mp 79°-80 C.

1. customPartition the mixture between ethyl ether and water
2. customseparate the organic phase
3. dry with materialdry (MgSO4)
4. filtrationFilter
5. customevaporate the solvent in vacuo
6. customto yield an oil
7. filtrationFilter through silica gel
8. washelute with 10% ethyl acetate/hexane
9. customto yield a crude solid
10. customRecrystallize (hexane, ethyl ether)