Tetrahydrofuran → HCID 59355026, compound

HRID 2196400Notes

Reaction equation

HRID 2196400 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

5

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 576172DIETHYL BENZYLSUCCINATEHCID 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)+.

Workup

  1. customThe reaction was quenched with H2O (15 mL)
  2. additiondiluted with Et2O (300 mL) and layers
  3. customseparated
  4. concentrationThe organic layer was concentrated under vacuum
  5. customthe resulting residue recrystallized from EtOH)(0°)

Sources & evidence

ORD record
ord-5df50a6e9bcf4a10b62d1b3d7aac7451
Source dataset
uspto-grants-2012_12
Patent number
US08338434B2

Reaction notes

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