Reacción #6588

Ecuación de reacción

N-methoxy-N-methylbenzamide

lithium hexamethyldisilazane

3-benzyloxyphenylacetylene

→

title compound

Rendimiento 57.0%

1-Phenyl-3-(3-benzyloxyphenyl)-2-propyne-1-one

Rendimiento 57.0%

Disolventes

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONAdd, by dropwise addition
2. 2
   OtroRemove the cooling bath
3. 3
   workup.STIRRINGstir at room temperature for 1 hour
4. 4
   OtroPartition between ethyl ether and water
5. 5
   Otroseparate the organic phase
6. 6
   Secadodry (MgSO4)
7. 7
   FiltraciónFilter
8. 8
   Otroevaporate the solvent in vacuo
9. 9
   Otroto yield a crude solid
10. 10
    OtroRecrystallize (hexane/ethyl acetate)

Procedimiento

Place lithium hexamethyldisilazane (15 mL of a 1M solution in tetrahydrofuran, 15 mmol) and tetrahydrofuran (75 mL) under an argon atmosphere and cool with an ice-water bath. Add, by dropwise addition, a solution of 3-benzyloxyphenylacetylene (3.13 g, 15 mmol) in tetrahydrofuran. Stir at 0° C. for 45 minutes, then add, by dropwise addition, N-methoxy-N-methylbenzamide (2.45 mL, 16 mmol). Remove the cooling bath and stir at room temperature for 1 hour. Partition between ethyl ether and water, separate the organic phase and dry (MgSO4). Filter and evaporate the solvent in vacuo to yield a crude solid. Recrystallize (hexane/ethyl acetate) to yield 2.67 g (57%) of the title compound; mp 75°-77° C.

Fuente