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: LCMS (ES) m/z 410 (M+H)+.