Ethyl cyanoacetate → Ethyl 2-chloro-2-cyano-3-methyl-5-oxopentanoate

HRID 2396582Notes

Reaction equation

HRID 2396582 reaction equation
[Cl:1][C:2]([C:12]#[N:13])([CH2:8][CH2:9][CH:10]=[O:11])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:14](CC(OCC)=O)#N.ClC(Cl)(C#N)C(OCC)=O.C([O-])([O-])=O.[K+].[K+].C(=O)/C=C/C>CCOC(C)=O>[Cl:1][C:2]([C:12]#[N:13])([CH:8]([CH3:14])[CH2:9][CH:10]=[O:11])[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

7

Reactant 5

HCID 7764Ethyl cyanoacetateHCID 11430Potassium CarbonateHCID 447466CrotonaldehydeHCID 10997655Ethyl dichlorocyanoacetateHCID 10998104Ethyl 2-chloro-2-cyano-5-oxopentanoate

Product 1

HCID 10867727Ethyl 2-chloro-2-cyano-3-methyl-5-oxopentanoateYield 34%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Following the procedure for the preparation of ethyl 2-chloro-2-cyano-5-oxopentanoate (Example 1), 37.6 g of ethyl cyanoacetate, 60.5 g of ethyl dichlorocyanoacetate, 350 mL of EtOAc, 1.7 g of K2CO3, and 56 mL of crotonaldehyde were allowed to react for an extended period of time. The title compound was obtained in 34% yield after workup and distillation (b.p. 115° C./1.0 mm Hg).

Workup

  1. customto react for an extended period of time

Sources & evidence

ORD record
ord-e3a2ecc3c362403daf7dfc0786a1dddf
Source dataset
uspto-grants-1996_02
Patent number
US05493028

Reaction notes

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