Reaktion #1159410

Reaktionsgleichung

5-formyl-2-methoxybenzeneboronic acid

2-methyl-5-bromobenzoxazole

K2CO3

→

title compound

Ausbeute 89.6%

4-methoxy-3-(2-methylbenzoxazol-5-yl)benzenecarboxaldehyde

Ausbeute 89.6%

Lösungsmittel

ethanol

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was refluxed for 20 hours
2. 2
   Temperaturthen cooled
3. 3
   Filtrationfiltered through diatomaceous earth
4. 4
   EinengenThe filtrate was concentrated in vacuo
5. 5
   Extraktionextracted with ethyl acetate
6. 6
   Waschenwashed with water
7. 7
   Trocknenthe organic layer dried over sodium sulphate
8. 8
   SonstigeThe crude was purified by column chromatography (heptane/ethyl acetate 7/3 to 6/4)

Vorschrift

A solution of 5-formyl-2-methoxybenzeneboronic acid (1 g, 5.6 mmol), 2-methyl-5-bromobenzoxazole (1 g, 4.72 mmol) and K2CO3 (1.63 g, 11.8 mmol) in ethanol (20 mL) and toluene (40 mL) was degassed prior to addition of Pd(Ph3)4 (55 mg, 0.047 mmol). The mixture was refluxed for 20 hours then cooled and filtered through diatomaceous earth. The filtrate was concentrated in vacuo, extracted with ethyl acetate, washed with water and the organic layer dried over sodium sulphate. The crude was purified by column chromatography (heptane/ethyl acetate 7/3 to 6/4) to give 1.13 g of title compound.

Quelle