Ethyl oxoacetate → ethyl (2E)-5-chloro-4-oxo-2-pentenoate

HRID 2376001Notes

Reaction equation

HRID 2376001 reaction equation
[Cl:1][CH2:2][C:3]([CH:5]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:4].[C:25]([O:29][CH2:30][CH3:31])(=[O:28])[CH:26]=O>O1CCOCC1>[Cl:1][CH2:2][C:3](=[O:4])/[CH:5]=[CH:26]/[C:25]([O:29][CH2:30][CH3:31])=[O:28]

Participants

4

Reactant 2

HCID 70211Ethyl oxoacetateHCID 2870041-Chloro-3-(triphenyl phosphoranylidene)propan-2-one

Product 1

HCID 86603623ethyl (2E)-5-chloro-4-oxo-2-pentenoateYield 47.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The mixture of 1-chloro-3-(triphenylphosphoranylidene)acetone (6.6 g) and ethyl glyoxylate (50% in toluene, 4.6 g) in dioxane (66 mL) was stirred at 80′ for 1.5 hour. The solvent was removed by concentration. The residue was purified by column chromatography on silica gel using a mixture of chloroform and hexane (1:1 v/v) as an eluent. The eluted fractions containing the desired product were collected and evaporated in vacuo to give ethyl (2E)-5-chloro-4-oxo-2-pentenoate (1.58 g).

Workup

  1. customThe solvent was removed by concentration
  2. customThe residue was purified by column chromatography on silica gel using
  3. additiona mixture of chloroform and hexane (1:1 v/v) as an eluent
  4. additionThe eluted fractions containing the desired product
  5. customwere collected
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-93f5dee9e46d44bc90d83ac634c41d90
Source dataset
uspto-grants-2008_12
Patent number
US07465731B2

Reaction notes

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