Potassium Carbonate → 1-[4-(2-Hydroxyethyl)phenyl]-2-pyrrolidinone
Reaction equation
CN(CC)C.C([O-])([O-])=O.[K+].[K+].[NH:12]1[CH2:16][CH2:15][CH2:14][C:13]1=[O:17].Br[C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][OH:27])=[CH:21][CH:20]=1>[Cu]I>[OH:27][CH2:26][CH2:25][C:22]1[CH:23]=[CH:24][C:19]([N:12]2[CH2:16][CH2:15][CH2:14][C:13]2=[O:17])=[CH:20][CH:21]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 130 °C
Procedure
A mixture of CuI (0.198 mmol), N,N-dimethylethylamine (0.398 mmol), K2CO3 (3.98 mmol) and pyrrolidin-2-one (3.98 mmol) was purged with nitrogen gas. 2-(4-bromophenyl)ethanol (1.99 mmol) was added and the mixture was purged with purged again with nitrogen. The reaction mixture was stirred at 130° C. overnight. After cooling to room temperature, the reaction mixture was diluted with water (25 mL), NH4OH (5 mL) and the aqueous layer was extracted with dichloromethane (3×40 mL). The combined organic extracts were dried over sodium sulfate and evaporated under reduced pressure; the crude was purified by column chromatography to afford the final product. Yield=37%.
Workup
- customwas purged with nitrogen gas
- customthe mixture was purged
- customwith purged again with nitrogen
- temperatureAfter cooling to room temperature
- additionthe reaction mixture was diluted with water (25 mL), NH4OH (5 mL)
- extractionthe aqueous layer was extracted with dichloromethane (3×40 mL)
- dry with materialThe combined organic extracts were dried over sodium sulfate
- customevaporated under reduced pressure
- customthe crude was purified by column chromatography
Sources & evidence
- ORD record
- ord-cac7aea0fdfc45639101761658c312fb
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08722720B2
Reaction notes
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