2-(Dimethylamino)ethanol → 4-benzyloxy-1-{4-[2-(dimethylamino)ethoxy]phenyl}-1H-pyridin-2-one

HRID 15033

Reaktionsgleichung

Reaktionsgleichung von HRID 15033
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)[C:11](=[O:22])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:23][N:24]([CH3:28])[CH2:25][CH2:26]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:15]2[CH:16]=[CH:17][C:18]([O:21][CH2:26][CH2:25][N:24]([CH3:28])[CH3:23])=[CH:19][CH:20]=2)[C:11](=[O:22])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 79022-(Dimethylamino)ethanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 684312834-benzyloxy-1-(4-hydroxyphenyl)-1H-pyridin-2-one

Produkt 1

HCID 115596254-benzyloxy-1-{4-[2-(dimethylamino)ethoxy]phenyl}-1H-pyridin-2-oneAusbeute 66,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

4-Benzyloxy-1-(4-hydroxyphenyl)-1H-pyridin-2-one (150 mg, 0.511 mmol), 2-(dimethylamino)ethanol (0.057 mL, 0.562 mmol), triphenylphosphine (269 mg, 1.02 mmols) and diethyl azodicarboxylate (0.163 mL, 1.02 mmols) were stirred overnight in THF (4 mL). Concentrating the reaction liquid under reduced pressure, the resulting residue was purified on silica gel column chromatography (C-300, methanol: chloroform=1:20-1:10) to provide the title compound (124 mg, 60%).

Aufarbeitung

  1. concentrationConcentrating
  2. customthe reaction liquid under reduced pressure
  3. customthe resulting residue was purified on silica gel column chromatography (C-300, methanol: chloroform=1:20-1:10)

Quellen und Nachweise

ORD-Eintrag
ord-03e023041a31460a9e95a92d281c2f32
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732456B2

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