Tributylphosphine → Methyl 5-[3-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]nicotinate

HRID 1294150Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1294150
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:16]=[C:17]([CH2:21][OH:22])[CH:18]=[CH:19][CH:20]=1.O[C:24]1[CH:25]=[N:26][CH:27]=[C:28]([CH:33]=1)[C:29]([O:31][CH3:32])=[O:30].C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:16]=[C:17]([CH:18]=[CH:19][CH:20]=1)[CH2:21][O:22][C:24]1[CH:25]=[N:26][CH:27]=[C:28]([CH:33]=1)[C:29]([O:31][CH3:32])=[O:30]

Komponenten

6

Edukt 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 354317Methyl 5-hydroxypyridine-3-carboxylateHCID 11140977{3-[(5-Methyl-2-Phenyl-1,3-Oxazol-4-Yl)methoxy]phenyl}methanol

Produkt 1

HCID 68885855Methyl 5-[3-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]nicotinateAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of [3-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]phenyl]methanol (1.92 g), methyl 5-hydroxynicotinate (1.0 g), tributylphosphine (1.98 g) and tetrahydrofuran (100 mL) was added 1,1′-(azodicarbonyl)dipiperidine (2.47 g) at room temperature and the mixture was stirred for 15 hrs. The precipitated crystals were removed by filtration. The filtrate was concentrated and the residue was subjected to silica gel column chromatography to give crystals (2.21 g, 79%) of methyl 5-[3-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]nicotinate from a fraction eluted with ethyl acetate-hexane (1:3, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 96-97° C.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-58abafe5bda94b8cb15af00f52df358f
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07238716B2

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