Реакция #321754

Уравнение реакции

2-(4-hexylphenyl)-5-(4-hydroxyphenyl)thiazole

hexanoic acid

N,N'-dicyclohexylcarbodiimide

4-pyrrolidinopyridine

→

2-(4-hexylphenyl)-5-(4-hexanoyloxyphenyl)thiazole

Выход 70.1%

Растворители

dichloromethane

Условия реакции

Обработка

1. 1
   workup.ADDITIONmixed
2. 2
   workup.STIRRINGby further stirring for 7 hours at room temperature
3. 3
   Другоеto precipitate N,N'-dicyclohexylurea
4. 4
   ФильтрацияThe resultant N,N'-dicyclohexylurea was filtered off
5. 5
   ДругоеThe residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=100/1)
6. 6
   Другоеrecrystallized from a mixture solvent of toluene-methanol

Методика

In a 200 ml-round-bottomed flask, 2.00 g (5.93 mM) of 2-(4-hexylphenyl)-5-(4-hydroxyphenyl)thiazole, 0.76 g (6.54 mM) of hexanoic acid and 40 ml of dichloromethane were placed and mixed. To the solution, 1.24 g (6.01 mM) of N,N'-dicyclohexylcarbodiimide and 0.10 g of 4-pyrrolidinopyridine were successively added under stirring at room temperature, followed by further stirring for 7 hours at room temperature to precipitate N,N'-dicyclohexylurea. The resultant N,N'-dicyclohexylurea was filtered off and the solvent of the filtrate was distilled-off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=100/1) and recrystallized from a mixture solvent of toluene-methanol to obtain 1.81 g of 2-(4-hexylphenyl)-5-(4-hexanoyloxyphenyl)thiazole (Yield: 70.1%). ##STR198##

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