Tributylphosphine → 4-[(Methoxymethoxy)methyl]-5-({4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenoxy}methyl)-2-phenyl-1,3-oxazole

HRID 2221803Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2221803
[CH3:1][O:2][CH2:3][O:4][CH2:5][C:6]1[N:7]=[C:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:9][C:10]=1[CH:11]=[O:12].C(P(CCCC)CCCC)CCC.[CH3:32][C:33]1[O:37][C:36]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[N:35][C:34]=1[CH2:44][O:45][C:46]1[CH:51]=[CH:50][C:49](O)=[CH:48][CH:47]=1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1>[CH3:1][O:2][CH2:3][O:4][CH2:5][C:6]1[N:7]=[C:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:9][C:10]=1[CH2:11][O:12][C:49]1[CH:48]=[CH:47][C:46]([O:45][CH2:44][C:34]2[N:35]=[C:36]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[O:37][C:33]=2[CH3:32])=[CH:51][CH:50]=1

Komponenten

6

Edukt 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 114592744-[(Methoxymethoxy)methyl]-2-phenyl-1,3-oxazole-5-carbaldehydeHCID 68884209HCID 68884209, Verbindung

Produkt 1

HCID 692174854-[(Methoxymethoxy)methyl]-5-({4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenoxy}methyl)-2-phenyl-1,3-oxazoleAusbeute 57,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of 4-[(methoxymethoxy)methyl]-2-phenyl-1,3-oxazole-5-carbaldehyde (0.45 g), tributylphosphine (0.73 g), 4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenol (0.50 g) and tetrahydrofuran (50 mL) was added 1,1′-(azodicarbonyl)dipiperidine (0.91 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 4-[(methoxymethoxy)methyl]-5-({4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenoxy}methyl)-2-phenyl-1,3-oxazole as colorless crystals (0.52 g, yield 57%) from a fraction eluted with ethyl acetate-hexane (1:2, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 74-75° C.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-1a9aef730f4043bba91c1e97fde8e779
Quelldatensatz
uspto-grants-2008_05
Patentnummer
US07368578B2

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