Tributylphosphine → 3-({3-methoxy-4-[(2-morpholin-4-yl-1,3-thiazol-4-yl)methoxy]benzyl}oxy)-1-phenyl-1H-pyrazole-4-carbaldehyde

HRID 2221888Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2221888
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:22][OH:23])[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]1[N:12]=[C:13]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[S:14][CH:15]=1.O[C:25]1[C:29]([CH:30]=[O:31])=[CH:28][N:27]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:26]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]1[N:12]=[C:13]([N:16]2[CH2:17][CH2:18][O:19][CH2:20][CH2:21]2)[S:14][CH:15]=1)[CH2:22][O:23][C:25]1[C:29]([CH:30]=[O:31])=[CH:28][N:27]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[N:26]=1

Komponenten

6

Edukt 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 69217104{3-Methoxy-4-[(2-morpholin-4-yl-1,3-thiazol-4-yl)methoxy]phenyl}methanolHCID 178519806HCID 178519806, Verbindung

Produkt 1

HCID 230765713-({3-methoxy-4-[(2-morpholin-4-yl-1,3-thiazol-4-yl)methoxy]benzyl}oxy)-1-phenyl-1H-pyrazole-4-carbaldehydeAusbeute 59,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of {3-methoxy-4-[(2-morpholin-4-yl-1,3-thiazol-4-yl)methoxy]phenyl}methanol (0.93 g), 3-hydroxy-1-phenyl-1H-pyrazole-4-carbaldehyde (0.58 g), tributylphosphine (0.85 g) and tetrahydrofuran (100 mL) was added 1,1′-(azodicarbonyl)dipiperidine (1.06 g) at room temperature, and the mixture was stirred for 15 hrs. The precipitated crystals were removed by filtration and the filtrate was concentrated. The residue was subjected to silica gel column chromatography to give 3-({3-methoxy-4-[(2-morpholin-4-yl-1,3-thiazol-4-yl)methoxy]benzyl}oxy)-1-phenyl-1H-pyrazole-4-carbaldehyde as crystals (0.83 g, yield 58%) from a fraction eluted with ethyl acetate-hexane (2:3, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 128-129° C.

Aufarbeitung

  1. customThe precipitated crystals were removed by filtration
  2. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-e001ebc39d5e4c6baae481f68e2de542
Quelldatensatz
uspto-grants-2008_05
Patentnummer
US07368578B2

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