Triphenylphosphine → Methyl 2-[2-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethyl]benzyloxy]phenyl]acetate

HRID 1294319

Reaktionsgleichung

Reaktionsgleichung von HRID 1294319
[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][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][OH:22])=[CH:17][CH:16]=1.O[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH2:30][C:31]([O:33][CH3:34])=[O:32].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1(C)C=CC=CC=1.C(OCC)(=O)C.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][CH2:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:21][O:22][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH2:30][C:31]([O:33][CH3:34])=[O:32])=[CH:19][CH:20]=1

Komponenten

8

Edukt 4

HCID 11776TriphenylphosphineHCID 89719Methyl (2-hydroxyphenyl)acetateHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 545680024-[2-(5-Methyl-2-phenyl-4-oxazolyl)ethyl]benzyl alcohol

Produkt 1

HCID 68886924Methyl 2-[2-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethyl]benzyloxy]phenyl]acetateAusbeute 59,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1140TolueneLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a mixture of [4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethyl]phenyl]methanol (0.60 g), methyl 2-(2-hydroxyphenyl)acetate (0.35 g), triphenylphosphine (0.79 g) and tetrahydrofuran (50 mL) was dropwise added a solution (40%, 1.39 g) of diethyl azodicarboxylate in toluene at room temperature, and the mixture was stirred for 15 hrs. To the reaction mixture was added ethyl acetate, the mixture was washed successively with water, a 2N aqueous sodium hydroxide solution and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give methyl 2-[2-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethyl]benzyloxy]phenyl]acetate as a colorless oil (0.54 g, 58%) from a fraction eluted with ethyl acetate-hexane (1:6, v/v).

Aufarbeitung

  1. washthe mixture was washed successively with water
  2. dry with materiala 2N aqueous sodium hydroxide solution and saturated brine, dried over anhydrous magnesium sulfate
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-ea41b0977d954d79a1146ad725b4919c
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07238716B2

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