Acrolein → Ethyl 2-chloro-2-cyano-5-oxopentanoate

HRID 2396578Notes

Reaction equation

HRID 2396578 reaction equation
[Cl:1][CH:2]([C:8]#[N:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH:10]([CH:12]=[CH2:13])=[O:11]>CCOC(C)=O.CC([O-])=O.[Na+]>[Cl:1][C:2]([C:8]#[N:9])([CH2:13][CH2:12][CH:10]=[O:11])[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

5

Reactant 2

HCID 7847AcroleinHCID 554591Ethyl chlorocyanoacetate

Product 1

HCID 10998104Ethyl 2-chloro-2-cyano-5-oxopentanoateYield 77.2%

Reagents, catalysts & solvents 2

HCID 517045Sodium AcetateCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
35 °C

Procedure

To a suspension of NaOAc (0.492 g, 6 mmol) in 200 mL of EtOAc were added at 5° C., 31.0 g (210 mmol) of ethyl chlorocyanoacetate and acrolein (14 g, 250 mmol). The resulting mixture was stirred at 35° C. for 16 hours, filtered, concentrated and distilled to give 33 g of the title compound (77%).

Workup

  1. additionwere added at 5° C.
  2. filtrationfiltered
  3. concentrationconcentrated
  4. distillationdistilled

Sources & evidence

ORD record
ord-8749493cbb504f49a00c7591c995599d
Source dataset
uspto-grants-1996_02
Patent number
US05493028

Reaction notes

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