反应 #6594

反应方程式

N-methoxy-N-methylbenzamide

lithium hexamethyldisilazane

3-(4-(dimethylamino)benzyloxy)phenylacetylene

→

title compound

1-Phenyl-3-[3-(4-(dimethylamino)benzyloxy)phenyl]-2-propyne-1-one

溶剂

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

反应条件

后处理

1. 1
   workup.STIRRINGstir at room temperature for 1 hour
2. 2
   其他Partition the mixture between ethyl ether and water
3. 3
   其他separate the organic phase
4. 4
   干燥dry (MgSO4)
5. 5
   过滤Filter
6. 6
   其他evaporate the solvent in vacuo
7. 7
   其他to yield an oil
8. 8
   过滤Filter through silica gel
9. 9
   洗涤elute with 10% ethyl acetate/hexane
10. 10
    其他to yield a crude solid
11. 11
    其他Purify by silica gel chromatography

实验过程

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-(4-(dimethylamino)benzyloxy)phenylacetylene (0.51 g, 2 mmol) in tetrahydrofuran and stir the solution for 45 minutes at 0° C. Add N-methoxy-N-methylbenzamide (0.4 g, 2.4 mmol), remove the cooling bath and stir 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. Purify by silica gel chromatography to give the title compound.

来源