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]>C1COCC1>[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
- 10 °C
Procedure
A mixture of ethyl 2-chloroacetate (110.0 g; 897.6 mmol) and ethyl formate (73.14 g; 987.4 mmol) was added slowly to a suspension of potassium t-butoxide (110.8 g; 987.4 mmol) in THF (1000 mL) at −5° C. (maintaining the temperature<10° C.) with mechanical stirring. The mixture was stirred at ambient temperature for 24 hours. The solids were collected by filtration and washed with THF (200 mL) and acetonitrile (200 mL). The material was dried under vacuum to give the product (152.7 g) which was used without further purification.
Workup
- filtrationThe solids were collected by filtration
- washwashed with THF (200 mL) and acetonitrile (200 mL)
- customThe material was dried under vacuum
Sources & evidence
- ORD record
- ord-2ea6dfb85e38424b9b824e1f31329a2f
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08841455B2
Reaction notes
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