Ethyl vinyl ether → HCID 54481174, compound
Reaction equation
[CH:1]([O:3][CH2:4][CH3:5])=[CH2:2].Cl[C:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:8]>>[CH2:1]([O:3][CH:4]=[CH:5][C:7](=[O:8])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH3:2]Participants
Procedure
145 g of ethyl vinyl ether were added dropwise to 137 g of ethyl chloroformylformate with cooling using ice/common salt; after warming to room temperature, the mixture was stirred for a further 20 hours. The volatile components were removed by distillation, and the residue was fractionated in a water-pump vacuum. Ethyl 4-ethoxy-2-oxobut-3-enoate of boiling point 140°-143° C./13 torr were obtained. 17.5 g of product were dissolved in 200 ml of toluene. 17.5 g of 2,6-dichlorophenylhydrazine were added at 0° C. were stirring. The mixture was slowly heated to boiling, and ethanol and water were removed in a water separator until the boiling point remained constant at 111° C. The residue was diluted with toluene, washed twice with 2 N hydrochloric acid, saturated hydrogen carbonate solution and water, dried, evaporated to dryness and recrystallized from ethanol. Yield: 18.3 g. Melting point: 51°-53° C.
Workup
- temperaturewith cooling
- customThe volatile components were removed by distillation
Sources & evidence
- ORD record
- ord-4532ea24e6554dc794fbd75de93b0722
- Source dataset
- uspto-grants-1990_01
- Patent number
- US04891057
Reaction notes
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