Diethyl propylmalonate → Diethyl 2-(5-phthalimidopentyl)-2-propylmalonate

HRID 325811Notes

Reaction equation

HRID 325811 reaction equation
[Na].[CH2:2]([CH:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:3][CH3:4].Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][N:22]1[C:26](=[O:27])[C:25]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:24]2[C:23]1=[O:32]>C(O)C>[C:26]1(=[O:27])[N:22]([CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][C:5]([CH2:2][CH2:3][CH3:4])([C:6]([O:8][CH2:9][CH3:10])=[O:7])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:23](=[O:32])[C:24]2=[CH:31][CH:30]=[CH:29][CH:28]=[C:25]12

Participants

5

Reactant 3

HCID 16552Diethyl propylmalonateHCID 136770N-(5-Bromopentyl)phthalimideHCID 5360545Sodium

Product 1

HCID 13313505Diethyl 2-(5-phthalimidopentyl)-2-propylmalonateYield 41%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium (0.5 g) was dissolved in ethanol (7 ml) and diethyl propylmalonate (4.4 g) was added to the solution. The resulting mixture was heated under reflux for 15 minutes. To the mixture was added N-(5-bromopentyl)phthalimide (6.4 g) and the mixture was further heated under reflux for 4 hours. Then, ethanol was removed by distillation. The residue was treated with ether and filtered. The filtrate was concentrated and the residue was chromatographed on silica gel column. A fraction eluted with 5% methanol in chloroform was recrystallized from a mixture of ether and hexane to give colorless crystals of diethyl 2-(5-phthalimidopentyl)-2-propylmalonate (m.p. 51°-52° C., yield 3.7 g).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 15 minutes
  3. temperaturethe mixture was further heated
  4. temperatureunder reflux for 4 hours
  5. customThen, ethanol was removed by distillation
  6. additionThe residue was treated with ether
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated
  9. customthe residue was chromatographed on silica gel column
  10. washA fraction eluted with 5% methanol in chloroform
  11. customwas recrystallized from a mixture of ether and hexane

Sources & evidence

ORD record
ord-43ffd1fe9a7042dc81c8e20b920519b2
Source dataset
uspto-grants-1984_04
Patent number
US04443365

Reaction notes

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