Diethyl ethylmalonate → Diethyl chloroethylmalonate

HRID 654607

Reaction equation

HRID 654607 reaction equation
[CH2:1]([CH:3]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].[Cl:14]C(Cl)(Cl)C(OCC)=O>O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(=O)([O-])[O-].[K+].[K+]>[Cl:14][C:3]([CH2:1][CH3:2])([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

5

Reactant 2

HCID 8610Diethyl ethylmalonateHCID 10588Ethyl trichloroacetate

Product 1

HCID 121803Diethyl chloroethylmalonateYield 70.1%

Reagents, catalysts & solvents 2

HCID 11430Potassium CarbonateCatalystHCID 11726816Tetrabutylammonium Fluoride TrihydrateCatalyst

Procedure

In a 10 mL round-bottom flask, 1.88 g of diethyl ethylmalonate (10 mmol), 2.10 g of ethyl trichloroacetate (11 mmol), 158 mg of tetra-n-butylammonium fluoride trihydrate (0.5 mmol), and 69 mg of potassium carbonate (0.5 mmol) were stirred at 24° C. for 5 h. After filtration, the solution was found to contain 1.56 g (70% yield) of diethyl α-chloro-α-ethylmalonate.

Workup

  1. filtrationAfter filtration

Sources & evidence

ORD record
ord-bf9b038c957d4ccf9eda320c0a3fec1a
Source dataset
uspto-grants-1992_07
Patent number
US05132475

Linked notes

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