3-[4-(3-Hydroxy-prop-1-ynyl)-phenyl]-1-(2-methyl-pyridin-4-yl)-3-o-tolyl-propan-1-one → 3-[4-(3-Hydroxy-propyl)-phenyl]-1-(2-methyl-pyridin-4-yl)-3-o-tolyl-propan-1-one

HRID 1617522Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1617522
[OH:1][CH2:2][C:3]#[C:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH3:28])[CH2:12][C:13]([C:15]2[CH:20]=[CH:19][N:18]=[C:17]([CH3:21])[CH:16]=2)=[O:14])=[CH:7][CH:6]=1>C(OCC)(=O)C.[Pd]>[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([CH:11]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH3:28])[CH2:12][C:13]([C:15]2[CH:20]=[CH:19][N:18]=[C:17]([CH3:21])[CH:16]=2)=[O:14])=[CH:9][CH:10]=1

Komponenten

4

Edukt 1

HCID 666687223-[4-(3-Hydroxy-prop-1-ynyl)-phenyl]-1-(2-methyl-pyridin-4-yl)-3-o-tolyl-propan-1-one

Produkt 1

HCID 670155883-[4-(3-Hydroxy-propyl)-phenyl]-1-(2-methyl-pyridin-4-yl)-3-o-tolyl-propan-1-oneAusbeute 101,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

3-[4-(3-Hydroxy-prop-1-ynyl)-phenyl]-1-(2-methyl-pyridin-4-yl)-3-o-tolyl-propan-1-one (example 85, step 1; 40 mg) in ethyl acetate (6 mL) was hydrogenated in the presence of Pd (5% on carbon, 7 mg) at room temperature for 1.5 hours. The solution was filtered over decalite, the filter residue was washed with ethyl acetate, and the solution was evaporated to yield 3-[4-(3-hydroxy-propyl)-phenyl]-1-(2-methyl-pyridin-4-yl)-3-o-tolyl-propan-1-one (41 mg, 64%) as a colorless oil, which was directly subjected to the next step.

Aufarbeitung

  1. filtrationThe solution was filtered over decalite
  2. washthe filter residue was washed with ethyl acetate
  3. customthe solution was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-f0f17e0a55bd45fa9c77315d4bb16254
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765730B2

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