Reacción #6587

Ecuación de reacción

phenylacetylene

N-methoxy-N-methylbenzamide

lithium diisopropylamide

tetrahydrofuran

→

title compound

Rendimiento 61.4%

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

Rendimiento 61.4%

Disolventes

cyclohexane

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroRemove the cooling bath
2. 2
   TemperaturaCool the yellow solution to 0° C.
3. 3
   OtroRemove the cooling bath
4. 4
   workup.STIRRINGstir for 30 minutes at room temperature
5. 5
   workup.ADDITIONPour onto ethyl ether and water
6. 6
   Otroseparate the organic phase
7. 7
   Secadodry (MgSO4)
8. 8
   FiltraciónFilter
9. 9
   Otroevaporate the solvent in vacuo
10. 10
    Otroto yield an oil
11. 11
    OtroPurify by silica gel chromatography (2% ethyl acetate/hexane)
12. 12
    workup.DISTILLATIONthen purify further by distillation (2×)

Procedimiento

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.

Fuente