Ethanol → 5-Ethoxy-2-pyrrolidinone
Reaction equation
[C:1]1(=[O:7])[NH:5][C:4](=[O:6])[CH2:3][CH2:2]1.B([O-])=O.[Na+].[OH-].[K+].[CH2:14](O)[CH3:15]>Cl>[CH2:14]([O:6][CH:4]1[NH:5][C:1](=[O:7])[CH2:2][CH2:3]1)[CH3:15]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
At 0° C., 9.91 g of succinimide were charged initially in 415 ml of ethanol and a total of 5.53 g of sodium boranate was added a little at a time. At this temperature, every 15 minutes 2 to 3 drops of 2N ethanolic hydrogen chloride were added dropwise over 4½ hours. Subsequently, the mixture was acidified to pH 3 using more acid. After stirring for 1 hour at 0° C., the mixture was neutralized using 1% strength ethanolic potassium hydroxide solution and the mixture was stirred for a further 15 minutes and evaporated. The residue was taken up in water and extracted three times with dichloromethane. After drying over sodium sulphate and concentrating, 7.16 g (55% of theory) of γ-ethoxy-γ-butyrolactam were obtained.
Workup
- stirringthe mixture was stirred for a further 15 minutes
- customevaporated
- extractionextracted three times with dichloromethane
- dry with materialAfter drying over sodium sulphate
- concentrationconcentrating
Sources & evidence
- ORD record
- ord-717292e4a4a341678bea3314ffdb385e
- Source dataset
- uspto-grants-2004_08
- Patent number
- US06770595B2
Reaction notes
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