Tetrahydrofuran → HCID 59355026, Verbindung

Reaktionsgleichung

[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]

Komponenten

Edukt 4

HCID 8028Tetrahydrofuran

HCID 24758Sodium hydride

HCID 576172Diethyl benzylsuccinate

HCID 22179298HCID 22179298, Verbindung

Produkt 1

HCID 59355026HCID 59355026, VerbindungAusbeute 64 %

Versuchsvorschrift

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: