Реакция #91678

Уравнение реакции

t-Butanol

DBU

adipic acid monomethyl ester

CDI

→

hexanedioic acid tert-butyl ester methyl ester

Выход 78.6%

Растворители

ether

DMF

Условия реакции

Обработка

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITproceeded at 40° C. for 70 hours
3. 3
   Промывкаthis mixture was washed with 10% aq. HOAc (100 mL), 10% aq. K2CO3 (100 mL), and water (3×100 mL)
4. 4
   Сушкаdried (MgSO4)
5. 5
   Другоеevaporated

Методика

To a solution of adipic acid monomethyl ester (4.8 g, 30 mmol) in DMF (30 mL), was added CDI (4.9 g, 30 mmol), and the resulting mixture was stirred under N2 at 40° C. for 1 hour. t-Butanol (4.4 g, 60 mmol) and DBU (4.6 g, 30 mmol) were added, and stirring proceeded at 40° C. for 70 hours. The mixture was poured into ether (100 mL), and this mixture was washed with 10% aq. HOAc (100 mL), 10% aq. K2CO3 (100 mL), and water (3×100 mL), dried (MgSO4), and evaporated, providing 5.1 g of hexanedioic acid tert-butyl ester methyl ester, in 78% yield; 1H NMR (CDCl3) δ 1.44 (s, 9H), 1.59-1.67 (m, 4H), 2.21-2.26 (m, 2H), 3.67 (s, 3H).

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