Acetic Acid → 4-[2-(5-Methyl-2-phenyl-4-oxazolyl)ethoxy]benzyl alcohol

HRID 233275

Reaktionsgleichung

Reaktionsgleichung von HRID 233275
[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][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][CH:17]=1.[BH4-].[Na+].C(O)(=O)C>C(O)C>[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][O:15][C:16]1[CH:17]=[CH:18][C:19]([CH2:20][OH:21])=[CH:22][CH:23]=1

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 107571064-[2-(5-Methyl-2-phenyloxazol-4-yl)ethoxy]benzaldehyde

Produkt 1

HCID 118338284-[2-(5-Methyl-2-phenyl-4-oxazolyl)ethoxy]benzyl alcoholAusbeute 97,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzaldehyde (7.0 g) in ethanol (100 ml) was added, under ice-cooling, sodium borohydride (0.473 g), and the mixture was stirred for 2 hours at room temperature. To the reaction mixture was added acetic acid (2 ml), which was poured into ice-water, then resulting crystalline precipitate was collected by filtration, followed by recrystallization from ethyl acetate--hexane to yield 4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzyl alcohol (6.9 g, 88%) as colorless plates, m.p.112°-113° C.

Aufarbeitung

  1. temperaturecooling
  2. filtrationresulting crystalline precipitate was collected by filtration
  3. customfollowed by recrystallization from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-195632b254084ab3a427680b29cd5744
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05591862

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