Reaktion #5377

Reaktionsgleichung

2-(4-decyloxyphenyl)-5-carboxybenzooxazole

octanol

4-pyrrolidinopyridine

→

2-(4-decyloxyphenyl)-5-octyloxycarbonyl benzooxazole

Ausbeute 49.3%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGby stirring for 8 hours at room temperature
2. 2
   Sonstigeto precipitate N,N'-dicyclohexylurea
3. 3
   FiltrationThe resultant N,N'-dicyclohexylurea was filtered off
4. 4
   Sonstigethe filtrate was dried under reduced pressure
5. 5
   SonstigeThe resultant was purified by silica gel column chromatography (eluent: toluene)
6. 6
   Sonstigerecrystallized twice from acetone

Vorschrift

In a 30 ml round-bottom flask, 0.30 g (0.76 m mole) of 2-(4-decyloxyphenyl)-5-carboxybenzooxazole, 0.11 g (0,84 m mole) of octanol and 8 ml of dichloromethane were placed. To the mixture solution 0.16 g (0.78 m mole) of N,N'-dicyclohexycarbodiimide and 0.04 g of 4-pyrrolidinopyridine were added in order under stirring at room temperature, followed by stirring for 8 hours at room temperature to precipitate N,N'-dicyclohexylurea. The resultant N,N'-dicyclohexylurea was filtered off and the filtrate was dried under reduced pressure. The resultant was purified by silica gel column chromatography (eluent: toluene) and recrystallized twice from acetone to obtain 0.19 g of 2-(4-decyloxyphenyl)-5-octyloxycarbonyl benzooxazole (Yield: 49.3%). ##STR89##

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