Reaction equation
[CH3:1][O:2][C:3](=[O:11])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9].C1N=CN(C(N2C=NC=C2)=O)C=1.[C:24](O)([CH3:27])([CH3:26])[CH3:25].C1CCN2C(=NCCC2)CC1>CN(C=O)C.CCOCC>[CH3:1][O:2][C:3](=[O:11])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]([O:10][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:9]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 40 °C
Procedure
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).
Workup
- stirringstirring
- waitproceeded at 40° C. for 70 hours
- washthis mixture was washed with 10% aq. HOAc (100 mL), 10% aq. K2CO3 (100 mL), and water (3×100 mL)
- dry with materialdried (MgSO4)
- customevaporated
Sources & evidence
- ORD record
- ord-a3d7ecaa7a4d404f803092b5cb53b354
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09447070B2
Linked notes
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