Ethyl chloroacetate → Potassium (E)-2-chloro-3-ethoxy-3-oxoprop-1-en-1-olate
Reaction equation
[Cl:1][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH:8](OCC)=[O:9].CC(C)([O-])C.[K+:18]>C(OC(C)C)(C)C>[Cl:1]/[C:2](/[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:8]/[O-:9].[K+:18]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
A mixture of ethyl 2-chloroacetate (220.8 g; 1802 mmol) and ethyl formate (133.5 g; 1802 mmol) was added slowly to a suspension of potassium t-butoxide (202.2 g; 1802 mmol) in diisopropyl ether (2000 mL) at 0° C. (maintaining the temperature<20° C.) with mechanical stirring. The mixture was stirred at ambient temperature for 24 hours. The solids were collected by filtration and washed with diisopropyl ether (500 mL) and acetonitrile (2×1500 mL). The material was dried under vacuum to give the product (270 g) which was used without further purification.
Workup
- filtrationThe solids were collected by filtration
- washwashed with diisopropyl ether (500 mL) and acetonitrile (2×1500 mL)
- customThe material was dried under vacuum
Sources & evidence
- ORD record
- ord-07b31b21b20c4bfa8097ae678bd050a1
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08841455B2
Reaction notes
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