4-Hydroxybenzaldehyde → 4-(2-Phenyl-4-oxazolylmethoxy)benzaldehyde

HRID 1720036Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1720036
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.CS(C)=O.ClC[C:16]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[NH:20][CH:19]=[CH:18][O:17]1.[C:27](=O)([O-])[O-].[Cs+].[Cs+]>O>[C:21]1([C:16]2[O:17][CH:18]=[C:19]([CH2:27][O:1][C:2]3[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=3)[N:20]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Komponenten

6

Edukt 4

HCID 1264-HydroxybenzaldehydeHCID 679Dimethyl SulfoxideHCID 10796Cesium carbonateHCID 224199112-(Chloromethyl)-2-phenyloxazole

Produkt 1

HCID 108265134-(2-Phenyl-4-oxazolylmethoxy)benzaldehydeAusbeute 90,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 4-hydroxybenzaldehyde (1.9 g, 17.0 mmol), dimethyl sulfoxide (50 mL), 2-(chloromethyl)-2-phenyloxazole (3.3 g, 17.0 mmol) and cesium carbonate (11.0 g, 34.0 mmol) was stirred at room temperature for 16 hours. The mixture was poured into water (400 mL) and filtration of the resultant precipitate afforded the crude product. Crystallization of the solids from ethyl acetate gave the product as a light yellow solid in 90.5 % yield, m.p. 94°-96° C. MS (EI, m/e): 279 (M)+

Aufarbeitung

  1. customafforded the crude product
  2. customCrystallization of the solids from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-7cd0b684c47d4a6696a0a569fe29c037
Quelldatensatz
uspto-grants-1996_04
Patentnummer
US05504097

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