Hydrochloric Acid → Cyclopentanecarboxylic acid, 1-methyl-2-oxo-, methyl ester
Reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]([CH:7]1[CH2:11][CH2:10][CH2:9][C:8]1=[O:12])=[O:6].[H][H].Cl.[CH3:16]N(C)C=O>>[CH3:16][C:7]1([C:5]([O:4][CH3:3])=[O:6])[CH2:11][CH2:10][CH2:9][C:8]1=[O:12]Participants
Procedure
2.52 g of sodium hydride (60% oily sodium hydride washed with anhydrous benzene) was added to 50 ml of anhydrous dimethylformamide under nitrogen atmosphere while stirring. 14.2 g of 2-methoxycarbonylcylopentanone was added to the mixture, followed by stirring at room temperature until generation of hydrogen was terminated. Next, 15 g of methyl iodide was added, and the mixture was stirred for a further 2 hours at 60° C. The reaction mixture thus obtained was poured into 300 ml of diluted hydrochloric acid solution and extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous sodium sulfate, followed by evaporation of the solvent under reduced pressure. The oily residue obtained was purified by vacuum distillation to obtain 14.5 g of the title compound.
Workup
- customwas terminated
- additionNext, 15 g of methyl iodide was added
- stirringthe mixture was stirred for a further 2 hours at 60° C
- customThe reaction mixture thus obtained
- extractionextracted with ethyl acetate
- washThe organic layer was washed with water
- dry with materialdried over anhydrous sodium sulfate
- customfollowed by evaporation of the solvent under reduced pressure
- customThe oily residue obtained
- distillationwas purified by vacuum distillation
Sources & evidence
- ORD record
- ord-7f67af60d10249f8a8ca99a0c74a7e97
- Source dataset
- uspto-grants-1996_05
- Patent number
- US05519160
Reaction notes
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