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

HRID 2221801Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2221801
[Si:1]([O:18][CH2:19][C:20]1[O:24][C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[N:22][C:21]=1[CH2:31][OH:32])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(P(CCCC)CCCC)CCC.[CH3:46][C:47]1[O:51][C:50]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)=[N:49][C:48]=1[CH2:58][O:59][C:60]1[CH:65]=[CH:64][C:63](O)=[CH:62][CH:61]=1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1>[Si:1]([O:18][CH2:19][C:20]1[O:24][C:23]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[N:22][C:21]=1[CH2:31][O:32][C:63]1[CH:62]=[CH:61][C:60]([O:59][CH2:58][C:48]2[N:49]=[C:50]([C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)[O:51][C:47]=2[CH3:46])=[CH:65][CH:64]=1)([C:14]([CH3:15])([CH3:16])[CH3:17])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 11189974[5-(Tert-butyldiphenylsilyloxymethyl)-2-phenyl-1,3-oxazol-4-yl]methanolHCID 68884209HCID 68884209, Verbindung

Produkt 1

HCID 692168795-(Tert-butyldiphenylsilyloxymethyl)-4-[[4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenoxy]methyl]-2-phenyl-1,3-oxazoleAusbeute 81,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of [5-(tert-butyldiphenylsilyloxymethyl)-2-phenyl-1,3-oxazol-4-yl]methanol (1.11 g), tributylphosphine (1.01 g), 4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenol (0.70 g) and tetrahydrofuran (80 mL) was added 1,1′-(azodicarbonyl)dipiperidine (1.26 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 5-(tert-butyldiphenylsilyloxymethyl)-4-[[4-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]phenoxy]methyl]-2-phenyl-1,3-oxazole as an oil (1.44 g, yield 81%) from a fraction eluted with ethyl acetate-hexane (1:4, v/v).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-a265c9a6385d46c7bc9756ab4e80dc19
Quelldatensatz
uspto-grants-2008_05
Patentnummer
US07368578B2

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