반응 #6586

반응 방정식

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

lithium hexamethyldisilazane

phenylacetylene

→

title compound

수율 34.9%

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

수율 34.9%

용매

tetrahydrofuran

tetrahydrofuran

반응 조건

후처리

1. 1
   기타Partition between ethyl ether and saturated aqueous sodium chloride
2. 2
   기타separate the organic phase
3. 3
   건조dry (MgSO4)
4. 4
   여과Filter
5. 5
   기타evaporate the solvent in vacuo
6. 6
   workup.ADDITIONPour onto silica gel
7. 7
   세척elute with 20% ethyl acetate/hexane
8. 8
   기타to yield a crude solid
9. 9
   기타Recrystallize (hexane/ethyl acetate)

실험 절차

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.

출처