反応 #6587

反応方程式

phenylacetylene

N-methoxy-N-methylbenzamide

lithium diisopropylamide

tetrahydrofuran

→

title compound

収率 61.4%

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

収率 61.4%

溶媒

cyclohexane

反応条件

後処理

1. 1
   その他Remove the cooling bath
2. 2
   温度Cool the yellow solution to 0° C.
3. 3
   その他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
   その他separate the organic phase
7. 7
   乾燥dry (MgSO4)
8. 8
   ろ過Filter
9. 9
   その他evaporate the solvent in vacuo
10. 10
    その他to yield an oil
11. 11
    その他Purify by silica gel chromatography (2% ethyl acetate/hexane)
12. 12
    workup.DISTILLATIONthen purify further by distillation (2×)

実験手順

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.

出典