Reaktion #1822884

Reaktionsgleichung

2-hydroxy-4-phenylthiazole

methyl (E)-β-methoxy-2-bromomethylcinnamate

→

methyl (E)-β-methoxy-2-(4-phenyl-2-thiazolyloxymethyl)cinnamate

Ausbeute 56.2%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe precipitate is filtered off
2. 2
   workup.ADDITIONthe DMF solution is poured into 100 ml of water
3. 3
   Extraktionthe mixture is extracted with methyl tert-butyl ether
4. 4
   SonstigeDrying
5. 5
   Sonstigeconcentration of the organic phase result in a brown oil which
6. 6
   Sonstigeis chromatographed on silica gel with cyclohexane/acetone (95:5)

Vorschrift

1.2 g (0.007 mol) of 2-hydroxy-4-phenylthiazole, 2.1 g (0.0077 mol) of silver carbonate and 2.1 g (0.0074 mol) of methyl (E)-β-methoxy-2-bromomethylcinnamate (see Example 2) are stirred in 15 ml of DMF at 60° C. for 8 hours. The precipitate is filtered off and the DMF solution is poured into 100 ml of water, and the mixture is extracted with methyl tert-butyl ether. Drying and concentration of the organic phase result in a brown oil which is chromatographed on silica gel with cyclohexane/acetone (95:5). 1.5 g (56% yield) of methyl (E)-β-methoxy-2-(4-phenyl-2-thiazolyloxymethyl)cinnamate as yellowish oil are isolated as the main fraction.

Quelle