Chloroacetone → Phthalimidoacetone

HRID 2117392Notes

Reaction equation

HRID 2117392 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[H-].[Na+].Cl[CH2:15][C:16](=[O:18])[CH3:17]>O1CCCC1>[O:18]=[C:16]([CH3:17])[CH2:15][N:5]1[C:1](=[O:11])[C:2]2[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4]1=[O:6]

Participants

5

Reactant 3

HCID 6571ChloroacetoneHCID 6809PhthalimideHCID 24758Sodium hydride

Product 1

HCID 235046PhthalimidoacetoneYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
40 °C

Procedure

Phthalimide (3 g) was dissolved in dry tetrahydrofuran (70 ml) and added dropwise at room temperature to a suspension of sodium hydride (539 mg) in tetrahydrofuran (15 ml). This was followed by heating at 40° C. for one hour, and then a solution of chloroacetone (1.99 g) dissolved in tetrahydrofuran (15 ml) was added dropwise. The mixture was then kept at the reflux temperature for 15 hours. After cooling, it was added to an ice/water mixture and extracted three times with ethyl acetate. The combined organic phases were washed once with saturated sodium chloride solution and then dried over magnesium sulfate. The solvent was removed in vacuo and the residue was chromatographed on silica gel (n-heptane/ethyl acetate 2:1). 2.9 g of the title compound were isolated.

Workup

  1. additionwas added dropwise
  2. temperatureAfter cooling
  3. extractionextracted three times with ethyl acetate
  4. washThe combined organic phases were washed once with saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was removed in vacuo
  7. customthe residue was chromatographed on silica gel (n-heptane/ethyl acetate 2:1)

Sources & evidence

ORD record
ord-45fe86296eed4f93889c190e5830bddb
Source dataset
uspto-grants-2008_10
Patent number
US07442717B2

Reaction notes

Loading…