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

HRID 226316Notes

Reaction equation

HRID 226316 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

Conditions

Temperature
80 °C

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° C. 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-1a47c4290dad4e84acaeabbd573d691b
Source dataset
uspto-grants-2009_07
Patent number
US07557127B2

Reaction notes

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