Reacción #6586

Ecuación de reacción

N-methoxy-N-methyl-(3,4,5-trimethoxy)benzamide

lithium hexamethyldisilazane

phenylacetylene

→

title compound

Rendimiento 34.9%

1-(3,4,5-Trimethoxyphenyl)-3-phenyl-2-propyne-1-one

Rendimiento 34.9%

Disolventes

tetrahydrofuran

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroPartition between ethyl ether and saturated aqueous sodium chloride
2. 2
   Otroseparate the organic phase
3. 3
   Secadodry (MgSO4)
4. 4
   FiltraciónFilter
5. 5
   Otroevaporate the solvent in vacuo
6. 6
   workup.ADDITIONPour onto silica gel
7. 7
   Lavadoelute with 20% ethyl acetate/hexane
8. 8
   Otroto yield a crude solid
9. 9
   OtroRecrystallize (hexane/ethyl acetate)

Procedimiento

Place lithium hexamethyldisilazane (3 mL of a 1M solution in tetrahydrofuran, 3 mmol) and tetrahydrofuran (10 mL) under an argon atmosphere and cool to 0° C. Add phenylacetylene (0.33 mL, 3 mmol) and stir at 0° C. for 30 minutes. Add N-methoxy-N-methyl-(3,4,5-trimethoxy)benzamide (0.76 g, 3 mmol), remove the cooling bath and stir at room temperature for 1 hour. Partition between ethyl ether and saturated aqueous sodium chloride, separate the organic phase and dry (MgSO4). Filter and evaporate the solvent in vacuo. Pour onto silica gel and elute with 20% ethyl acetate/hexane to yield a crude solid. Recrystallize (hexane/ethyl acetate) to yield 0.31 g of the title compound; mp 94°-96° C.

Fuente