Acetic Acid → Methyl 2-propylidene-4-chloroacetoacetate
Reaction equation
[CH3:1][O:2][C:3](=[O:9])[CH2:4][C:5]([CH2:7][Cl:8])=[O:6].[CH:10](=O)[CH2:11][CH3:12].C(O)(=O)C>ClCCl.N1CCCCC1>[CH3:1][O:2][C:3](=[O:9])[C:4](=[CH:10][CH2:11][CH3:12])[C:5]([CH2:7][Cl:8])=[O:6]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -27 °C
Procedure
To a solution of 4-chloroacetoacetic acid methyl ester (700 mg: 4.65 mMol.) and propionaldehyde (405 mg: 6.97 mMol.) and acetic acid (28 mg: 0.47 mMol.) in dichloromethane (3 ml) is added a solution of piperidine (24 mg: 0.28 mMol.) in dichloromethane (0.5 ml), and the mixture is stirred at -27° C. for 120 minutes. The reaction mixture is washed with dilute hydrochloric acid and water and concentrated under reduced pressure at lower than 15° C. to give 4-chloro-2-propylideneacetoacetic acid methyl ester (818 mg). Yield: 92%.
Workup
- washThe reaction mixture is washed with dilute hydrochloric acid and water
- concentrationconcentrated under reduced pressure at lower than 15° C.
Sources & evidence
- ORD record
- ord-3d6ff4ad7dda45e294602d21def90e23
- Source dataset
- uspto-grants-1994_10
- Patent number
- US05352792
Reaction notes
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