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

HRID 2221520Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2221520
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:25])=[C:9]([CH2:11][O:12][C:13]2[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][C:14]=2[O:21][CH2:22][O:23][CH3:24])[N:10]=1.C(O)C.[BH4-].[Na+].O>O1CCCC1>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[O:7][C:8]([CH3:25])=[C:9]([CH2:11][O:12][C:13]2[CH:20]=[CH:19][C:16]([CH2:17][OH:18])=[CH:15][C:14]=2[O:21][CH2:22][O:23][CH3:24])[N:10]=1

Komponenten

6

Edukt 4

HCID 702EthanolHCID 962WaterHCID 4311764Sodium borohydrideHCID 230766164-{[2-(2-Furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-(methoxymethoxy)benzaldehyde

Produkt 1

HCID 69215209(4-{[2-(2-Furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-(methoxymethoxy)phenyl)methanolAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-(methoxymethoxy)benzaldehyde (15.50 g) in tetrahydrofuran (100 mL)-ethanol (50 mL) was gradually added sodium borohydride (1.71 g) at 0° C. After stirring at room temperature for 2 hrs, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated to give (4-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-3-(methoxymethoxy)phenyl)methanol as colorless crystals (14.11 g, yield 91%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 92-93° C.

Aufarbeitung

  1. customat 0° C
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-cdaaf4d5ec7844848119589932aa5f07
Quelldatensatz
uspto-grants-2008_05
Patentnummer
US07368578B2

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