Water → 2-Chloro-3-oxo-pentanedioic acid diethyl ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:14])[CH2:5][C:6](=[O:13])[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:2].S(Cl)([Cl:18])(=O)=O.O>C(Cl)Cl>[CH2:11]([O:10][C:8](=[O:9])[CH:7]([Cl:18])[C:6](=[O:13])[CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:14])[CH3:12]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -9 °C
Procedure
Dissolve 3-oxo-pentanedioic acid diethyl ester (1122 g, 5.327 mol) in CH2Cl2 (3 L) and cool to −9° C. To the above solution, slowly add a solution of sulfuryl chloride (374 g, 2.69 mol) in CH2Cl2 (3 L) over 3 h. Upon completion, add a second charge of sulfuryl chloride (374 g, 2.69 mol) in CH2Cl2 (3 L) over 4 h. Stir the resulting cooled solution for one hour, then warm to room temperature and stir overnight. Cool the solution in an ice bath and slowly add water (8 L). Stir for 15 min, then separate the layers. Extract the aqueous layer with additional CH2Cl2. Combine the organic phases and wash with saturated NaHCO3 (3 L). Dry and concentrate the organic solution to obtain 1370 g (105%) of the title compound as a colorless oil. Use the material as-is in the next reaction without further purification. ES/MS m/z (35Cl) 235 [M−1]−.
Workup
- additionUpon completion, add
- temperaturecooled solution for one hour
- temperaturewarm to room temperature
- stirringstir overnight
- temperatureCool the solution in an ice bath
- stirringStir for 15 min
- customseparate the layers
- extractionExtract the aqueous layer with additional CH2Cl2
- washCombine the organic phases and wash with saturated NaHCO3 (3 L)
- customDry
- concentrationconcentrate the organic solution
Sources & evidence
- ORD record
- ord-d7d211d82ec94155ac7da3a8bf375dd6
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08049013B2
Reaction notes
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