Reacción #6584

Ecuación de reacción

N-methoxy-N-methylbenzamide

lithium hexamethyldisilazane

3-(4-methoxybenzyloxy)phenylacetylene

→

title compound

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

Disolventes

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGstir at room temperature for 1 hour
2. 2
   OtroPartition the mixture between ethyl ether and water
3. 3
   Otroseparate the organic phase
4. 4
   Secadodry (MgSO4)
5. 5
   FiltraciónFilter
6. 6
   Otroevaporate the solvent in vacuo
7. 7
   Otroto yield an oil
8. 8
   FiltraciónFilter through silica gel
9. 9
   Lavadoelute with 10% ethyl acetate/hexane
10. 10
    Otroto yield a crude solid
11. 11
    OtroRecrystallize (hexane, ethyl ether)

Procedimiento

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-methoxybenzyloxy)phenylacetylene (0.48 g, 2 mmol) in tetrahydrofuran and stir the brown 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. Recrystallize (hexane, ethyl ether) to yield 0.26 g (1st crop) and 0.15 g (2nd crop) of the title compound; mp 79°-80° C.

Fuente