Sulfuric Acid → [5-[2-[4-(5-Methyl-2-phenyl-4-oxazolyl)methoxyphenyl]ethyl]-2-phenyl-4-oxazolyl]methanol

HRID 2221614

Reaktionsgleichung

Reaktionsgleichung von HRID 2221614
[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:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23]2[O:27][C:26]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[N:25][C:24]=2[CH2:34][O:35]COC)=[CH:17][CH:16]=1.S(=O)(=O)(O)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:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23]2[O:27][C:26]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[N:25][C:24]=2[CH2:34][OH:35])=[CH:17][CH:16]=1

Komponenten

4

Edukt 2

HCID 1118Sulfuric AcidHCID 99361405-[2-[4-(5-Methyl-2-phenyl-4-oxazolyl)methoxyphenyl]ethyl]-4-methoxymethoxymethyl-2-phenyloxazole

Produkt 1

HCID 69217381[5-[2-[4-(5-Methyl-2-phenyl-4-oxazolyl)methoxyphenyl]ethyl]-2-phenyl-4-oxazolyl]methanolAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 5-{2-[4-(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxyphenyl]ethyl}-4-methoxymethoxymethyl-2-phenyloxazole (3.80 g), 10% sulfuric acid (10 mL) and tetrahydrofuran (100 mL) was refluxed for 2 hrs and concentrated. Ethyl acetate was poured into the residue, and the mixture was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give (5-{2-[4-(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxyphenyl]ethyl}-2-phenyl-1,3-oxazol-4-yl)methanol as colorless crystals (2.03 g, yield 59%) from a fraction eluted with ethyl acetate-hexane (1:2, v/v). The crystals were recrystallized from ethyl acetate-hexane. melting point: 142-143° C.

Aufarbeitung

  1. temperaturewas refluxed for 2 hrs
  2. concentrationconcentrated
  3. additionEthyl acetate was poured into the residue
  4. washthe mixture was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-99bea4ba3d1c42fe8b53f4f282e1abc0
Quelldatensatz
uspto-grants-2008_05
Patentnummer
US07368578B2

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