반응 #6587

반응 방정식

phenylacetylene

N-methoxy-N-methylbenzamide

lithium diisopropylamide

tetrahydrofuran

→

title compound

수율 61.4%

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

수율 61.4%

용매

cyclohexane

반응 조건

후처리

1. 1
   기타Remove the cooling bath
2. 2
   온도Cool the yellow solution to 0° C.
3. 3
   기타Remove the cooling bath
4. 4
   workup.STIRRINGstir for 30 minutes at room temperature
5. 5
   workup.ADDITIONPour onto ethyl ether and water
6. 6
   기타separate the organic phase
7. 7
   건조dry (MgSO4)
8. 8
   여과Filter
9. 9
   기타evaporate the solvent in vacuo
10. 10
    기타to yield an oil
11. 11
    기타Purify by silica gel chromatography (2% ethyl acetate/hexane)
12. 12
    workup.DISTILLATIONthen purify further by distillation (2×)

실험 절차

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.

출처