Tetrahydrofuran → HCID 59355026, compound

Reaction equation

[H-].[Na+].[C:3]1([CH2:9][CH:10]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.BrC[C:24]1[CH:34]=[CH:33][CH:32]=[C:26]2[C:27]([NH:29][C:30](=[O:31])[C:25]=12)=[O:28].[CH2:35]1COCC1>>[O:31]=[C:30]1[C:25]2[C:26](=[CH:32][CH:33]=[CH:34][CH:24]=2)[C:27](=[O:28])[N:29]1[CH2:35][C:10]([CH2:9][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

Reactant 4

HCID 8028Tetrahydrofuran

HCID 24758Sodium hydride

HCID 576172Diethyl benzylsuccinate

HCID 22179298HCID 22179298, compound

Product 1

HCID 59355026HCID 59355026, compoundYield 64%

Procedure

To a suspension of NaH (2.2 g, 54 mmole) in THF (200 mL) was added diethyl 2-(phenylmethyl)butanedioate (12.5 g, 49.9 mmole). After 30 min at RT, bromomethyl phthalimide was added to the reaction mixture and the contents were stirred for 14 h at RT. The reaction was quenched with H2O (15 mL), diluted with Et2O (300 mL) and layers separated. The organic layer was concentrated under vacuum and the resulting residue recrystallized from EtOH (0°) to give the title compound (13 g, 64%) as a white solid: