3-Hydroxybenzyl alcohol → (3-{[2-(2-Furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}phenyl)methanol

HRID 2221508Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2221508
Cl[CH2:2][C:3]1[N:4]=[C:5]([C:9]2[O:10][CH:11]=[CH:12][CH:13]=2)[O:6][C:7]=1[CH3:8].[OH:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH2:18][OH:19].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[O:10]1[CH:11]=[CH:12][CH:13]=[C:9]1[C:5]1[O:6][C:7]([CH3:8])=[C:3]([CH2:2][O:14][C:15]2[CH:16]=[C:17]([CH2:18][OH:19])[CH:20]=[CH:21][CH:22]=2)[N:4]=1

Komponenten

6

Edukt 4

HCID 1023-Hydroxybenzyl alcoholHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 223445824-(Chloromethyl)-2-(furan-2-yl)-5-methyl-1,3-oxazole

Produkt 1

HCID 69217134(3-{[2-(2-Furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}phenyl)methanolAusbeute 55,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 4-chloromethyl-2-(2-furyl)-5-methyl-1,3-oxazole (22.3 g), 3-hydroxybenzyl alcohol (10.0 g), potassium carbonate (11.14 g) and N,N-dimethylformamide (200 mL) was stirred at 90° C. for 4 hrs. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography, and eluted with ethyl acetate-hexane (1:1, v/v) to give (3-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}phenyl)methanol as colorless crystals (12.75 g, yield 55%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 100-101° C.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. washeluted with ethyl acetate-hexane (1:1

Quellen und Nachweise

ORD-Eintrag
ord-b1eca34375a54c12a89819457556ad6d
Quelldatensatz
uspto-grants-2008_05
Patentnummer
US07368578B2

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