Water → 3-Phenyl-propynoic acid phenyl-(3,4,5-trimethoxy-benzyl)-amide

HRID 1623471Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1623471
[C:1]1([NH:7][C:8](=[O:17])[C:9]#[C:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:19][C:20]1[CH:21]=[C:22]([O:30][CH3:31])[C:23]([O:28][CH3:29])=[C:24]([O:26][CH3:27])[CH:25]=1.C([O-])([O-])=O.[Cs+].[Cs+].O>CN(C=O)C>[C:1]1([N:7]([CH2:19][C:20]2[CH:21]=[C:22]([O:30][CH3:31])[C:23]([O:28][CH3:29])=[C:24]([O:26][CH3:27])[CH:25]=2)[C:8](=[O:17])[C:9]#[C:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 10796Cesium carbonateHCID 305965N,3-diphenylprop-2-ynamideHCID 103552715-(Bromomethyl)-1,2,3-trimethoxybenzene

Produkt 1

HCID 670362353-Phenyl-propynoic acid phenyl-(3,4,5-trimethoxy-benzyl)-amideAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

3-Phenyl-propynoic acid phenylamide (951.4 mg, 4.3 mmol), 5-bromomethyl-1,2,3-trimethoxy-benzene (1.35 g, 5.16 mmol), and Cs2CO3 (2.1 g, 6.45 mmol) were dissolved in DMF (20 ml). The mixture was stirred at room temperature for 16 h. The mixture was poured into water and extracted with ethyl acetate, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification was by flash column chromatography on silica gel, eluting with hexanes-EtOAc (6:1 and then 4:1) afforded 3-phenyl-propynoic acid phenyl-(3,4,5-trimethoxy-benzyl)-amide 1.03 g (65%).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customPurification
  5. washeluting with hexanes-EtOAc (6:1

Quellen und Nachweise

ORD-Eintrag
ord-5ca7e5b5e7fb40daac691d1c0f043b88
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08778973B2

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