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

HRID 6490

Reaktionsgleichung

Reaktionsgleichung von HRID 6490
C[Si](C)(C)N[Si](C)(C)C.[Li].[C:11]1([C:17]#[CH:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CON(C)[C:22](=[O:35])[C:23]1[CH:28]=[C:27]([O:29][CH3:30])[C:26]([O:31][CH3:32])=[C:25]([O:33][CH3:34])[CH:24]=1>O1CCCC1>[CH3:30][O:29][C:27]1[CH:28]=[C:23]([C:22](=[O:35])[C:18]#[C:17][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:24]=[C:25]([O:33][CH3:34])[C:26]=1[O:31][CH3:32]

Komponenten

5

Edukt 3

HCID 10821PhenylacetyleneHCID 267535N,3,4,5-tetramethoxy-N-methyl-BenzamideHCID 57426343Lithium bis(trimethylsilyl)amide

Produkt 1

HCID 147633891-(3,4,5-Trimethoxyphenyl)-3-phenyl-2-propyne-1-oneAusbeute 34,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  1. customPartition between ethyl ether and saturated aqueous sodium chloride
  2. customseparate the organic phase
  3. dry with materialdry (MgSO4)
  4. filtrationFilter
  5. customevaporate the solvent in vacuo
  6. additionPour onto silica gel
  7. washelute with 20% ethyl acetate/hexane
  8. customto yield a crude solid
  9. customRecrystallize (hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-49f779f24ab24cde9206b27accb4fa10
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05248825

Verknüpfte Notizen

Wird geladen…