N-3-Bromopropylphthalimide → Dibenzyl-2-(3-phthalimidopropyl)malonate

HRID 1953808Notes

Reaction equation

HRID 1953808 reaction equation
[C:1]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:13])[CH2:2][C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].[H-].[Na+].Br[CH2:25][CH2:26][CH2:27][N:28]1[C:32](=[O:33])[C:31]2=[CH:34][CH:35]=[CH:36][CH:37]=[C:30]2[C:29]1=[O:38]>C1COCC1>[CH2:6]([O:5][C:3](=[O:4])[CH:2]([CH2:25][CH2:26][CH2:27][N:28]1[C:32](=[O:33])[C:31]2=[CH:34][CH:35]=[CH:36][CH:37]=[C:30]2[C:29]1=[O:38])[C:1]([O:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 21611N-3-BromopropylphthalimideHCID 24758Sodium hydrideHCID 84754Dibenzyl malonate

Product 1

HCID 18533183Dibenzyl-2-(3-phthalimidopropyl)malonateYield 52.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of dibenzyl malonate (20 g) in anhydrous THF (200 ml) was treated at 0° C. with sodium hydride (60% dispersion in mineral oil, 3.1 g). The mixture was allowed to warm to room temperature and stirred for 30 minutes under nitrogen. The mixture was then treated with a solution of N-(3-bromopropyl)phthalimide (20.5 g) in THF (100 ml) and heated at reflux for 12 hours. The reaction was then cooled, filtered, and the filtrate evaporated in vacuo. The residue was partitioned between ethyl acetate (200 ml) and saturated aqueous ammonium chloride (150 ml). The organic layer was washed with water (100 ml), brine (100 ml), dried (MgSO4), filtered and the filtrate evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting with 20% ethyl acetate in hexane to yield the title compound (17.5 g, 50%) as a white solid.

Workup

  1. temperatureheated
  2. temperatureat reflux for 12 hours
  3. temperatureThe reaction was then cooled
  4. filtrationfiltered
  5. customthe filtrate evaporated in vacuo
  6. customThe residue was partitioned between ethyl acetate (200 ml) and saturated aqueous ammonium chloride (150 ml)
  7. washThe organic layer was washed with water (100 ml), brine (100 ml)
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customthe filtrate evaporated in vacuo
  11. customThe residue was purified by column chromatography on silica gel eluting with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-acf8cabc7b0a4bd18f54f9b8b4f83cbb
Source dataset
uspto-grants-2000_09
Patent number
US06118001

Reaction notes

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