反応 #91678

反応方程式

t-Butanol

DBU

adipic acid monomethyl ester

CDI

→

hexanedioic acid tert-butyl ester methyl ester

収率 78.6%

溶媒

ether

DMF

反応条件

後処理

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITproceeded at 40° C. for 70 hours
3. 3
   洗浄this mixture was washed with 10% aq. HOAc (100 mL), 10% aq. K2CO3 (100 mL), and water (3×100 mL)
4. 4
   乾燥dried (MgSO4)
5. 5
   その他evaporated

実験手順

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).

出典