反应 #6587

反应方程式

phenylacetylene

N-methoxy-N-methylbenzamide

lithium diisopropylamide

tetrahydrofuran

→

title compound

收率 61.4%

1-Phenyl-3-phenyl-2-propyne-1-one

收率 61.4%

溶剂

cyclohexane

反应条件

后处理

1. 1
   其他Remove the cooling bath
2. 2
   温度Cool the yellow solution to 0° C.
3. 3
   其他Remove the cooling bath
4. 4
   workup.STIRRINGstir for 30 minutes at room temperature
5. 5
   workup.ADDITIONPour onto ethyl ether and water
6. 6
   其他separate the organic phase
7. 7
   干燥dry (MgSO4)
8. 8
   过滤Filter
9. 9
   其他evaporate the solvent in vacuo
10. 10
    其他to yield an oil
11. 11
    其他Purify by silica gel chromatography (2% ethyl acetate/hexane)
12. 12
    workup.DISTILLATIONthen purify further by distillation (2×)

实验过程

Place lithium diisopropylamide (10 mL of a 1.5M solution in cyclohexane) and tetrahydrofuran (40 mL) under an argon atmosphere and cool to 0° C. Add, by dropwise addition, phenylacetylene (1.65 mL, 15 mmol). Remove the cooling bath and stir for 30 minutes as room temperature. Cool the yellow solution to 0° C. and add, by dropwise addition, N-methoxy-N-methylbenzamide (3.04 mL, 20 mmol). Remove the cooling bath and stir for 30 minutes at room temperature. Pour onto ethyl ether and water, separate the organic phase and dry (MgSO4). Filter and evaporate the solvent in vacuo to yield an oil. Purify by silica gel chromatography (2% ethyl acetate/hexane) then purify further by distillation (2×) to yield 1.9 g of the title compound; bp 210° C. in vacuo.

来源