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

HRID 2396573Notes

Reaction equation

HRID 2396573 reaction equation
C([O-])([O-])=O.[K+].[K+].[C:7]([CH2:9][C:10](OCC)=[O:11])#N.Cl[C:16]([Cl:24])([C:22]#[N:23])[C:17]([O:19][CH2:20][CH3:21])=[O:18].C(C=C)=O>C(OCC)(=O)C>[Cl:24][C:16]([C:22]#[N:23])([CH2:7][CH2:9][CH:10]=[O:11])[C:17]([O:19][CH2:20][CH3:21])=[O:18]

Participants

6

Reactant 4

HCID 7764Ethyl cyanoacetateHCID 7847AcroleinHCID 11430Potassium CarbonateHCID 10997655Ethyl dichlorocyanoacetate

Product 1

HCID 10998104Ethyl 2-chloro-2-cyano-5-oxopentanoateYield 77%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
5 °C

Procedure

To a suspension of finely ground K2CO3 (4.26 g, 30 mmol) in 100 mL of ethyl acetate were added sequentially 5.65 g of ethyl cyanoacetate (50 mmol) and 9.1 g of ethyl dichlorocyanoacetate (50 mmol) at 0° C. Acrolein (6.72 g, 120 mmol) was added within a period of 1 h using a syringe pump. The resulting mixture was stirred at 5° C. for 3 hours, filtered through Celite with the aid of CH2Cl2, concentrated (25° C., 25 mm Hg), and distilled to give 15.6 of the title compound (77%).

Workup

  1. filtrationfiltered through Celite with the aid of CH2Cl2
  2. concentrationconcentrated (25° C., 25 mm Hg)
  3. distillationdistilled

Sources & evidence

ORD record
ord-56ef6a3692c0487d81c6bafbb62323e0
Source dataset
uspto-grants-1996_02
Patent number
US05493028

Reaction notes

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