Ethanol → 5-Ethoxy-2-pyrrolidinone

HRID 2297076Notes

Reaction equation

HRID 2297076 reaction equation
[C:1]1(=[O:7])[NH:5][C:4](=[O:6])[CH2:3][CH2:2]1.[BH4-].[Na+].[OH-].[K+].[CH2:12](O)[CH3:13]>Cl>[CH2:12]([O:6][CH:4]1[NH:5][C:1](=[O:7])[CH2:2][CH2:3]1)[CH3:13]

Participants

6

Reactant 4

HCID 702EthanolHCID 11439SuccinimideHCID 14797Potassium HydroxideHCID 4311764Sodium borohydride

Product 1

HCID 35805555-Ethoxy-2-pyrrolidinoneYield 55%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidCatalyst

Procedure

At 0° C., 9.91 g of succinimide were initially charged in 415 ml of ethanol and admixed, a little at a time, with a total of 5.53 g of sodium borohydride. At this temperature, every 15 minutes 2 to 3 drops of 2N ethanolic hydrogen chloride were added dropwise over a period of 4½ hours. The mixture was subsequently acidified to pH 3 using more acid. The mixture was stirred at 0C for one hour and then neutralized with 1% strength ethanolic potassium hydroxide solution, stirred for a further 15 minutes and concentrated. The residue was taken up in water and extracted three times with dichloromethane. Drying over sodium sulphate and concentration gave 7.16 g (55% of theory) of γ-ethoxy-γ-butyrolactam.

Workup

  1. concentrationconcentrated
  2. extractionextracted three times with dichloromethane
  3. dry with materialDrying over sodium sulphate and concentration

Sources & evidence

ORD record
ord-76eb8b7028c74acb96da42b94a38e3b8
Source dataset
uspto-grants-2002_12
Patent number
US06489490B1

Reaction notes

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