Реакция #64670

Уравнение реакции

DCC

1,16-hexadecanedioic acid

N-hydroxyphthalimide

→

N-(15-carboxypentadecanoyloxy)phthalimide

Выход 41.1%

Растворители

tetrahydrofuran

tetrahydrofuran

Условия реакции

Обработка

1. 1
   workup.STIRRINGthe resulting mixture was stirred overnight
2. 2
   ФильтрацияThe reaction mixture was filtered
3. 3
   Концентрированиеthe filtrate was concentrated under reduced pressure
4. 4
   ДругоеThe residue was separated
5. 5
   Другоеpurified by silica gel chromatography

Методика

In 15 ml of anhydrous tetrahydrufuran 1,16-hexadecanedioic acid (500 mg, 1.75 mmoles) was dissolved. To the obtained solution, were added a solution of N-hydroxyphthalimide (285 mg, 1.75 mmoles) in 10 ml of anhydrous tetrahydrofuran and N,N-dimethylaminopyridine hydrochloride (1.4 mg) and the mixture was stirred for 30 minutes. To the mixture was added a solution of DCC (361 mg, 1.75 mmoles) in 3 ml of anhydrous tetrahydrofuran and the resulting mixture was stirred overnight. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was separated and purified by silica gel chromatography, to give N-(15-carboxypentadecanoyloxy)phthalimide (310 mg, 41%) having the following properties.

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