Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl ester → Ethyl 4-(4-chlorophenyl)-2-pentenoate

HRID 1440998Notes

Reaction equation

HRID 1440998 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:11])[CH:9]=O)=[CH:4][CH:3]=1.[C:12]([CH:17]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:14][CH2:15][CH3:16])=[O:13]>O1CCOCC1.C(OCC)(=O)C.CCCCCCC.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:11])[CH:9]=[CH:17][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 5870362-(4-Chlorophenyl)propanal

Product 1

HCID 54104672Ethyl 4-(4-chlorophenyl)-2-pentenoate

Reagents, catalysts & solvents 3

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolventHCID 21899848Ethylacetate heptaneSolvent

Procedure

To a stirred solution of 3.9 g (0.023 mole) of 2-(4-chlorophenyl)propionaldehyde in 25 mL of 1,4-dioxane is added in one portion 9.0 g (0.026 mole) of (carbethoxymethylene)triphenylphosphorane. The reaction mixture is stirred for approximately 16 hours at ambient temperature after which the solvent is evaporated under reduced pressure, leaving a residue which is then dissolved in ethyl acetate. Approximately 10 g of silica gel is mixed with the resulting solution. The solvent is evaporated from this mixture, and the residue is placed in a sintered glass filter. The silica gel is then eluted with 100 mL of heptane/ethyl acetate (3:1). These solvents are evaporated under reduced pressure, leaving a residue. This residue is dissolved in 30 mL of heptane/ethyl acetate (9:1), treated with 5 g of silica gel, and filtered. The filtrate is evaporated under reduced pressure, leaving ethyl 4-(4-chlorophenyl)-2-pentenoate as a residue.

Workup

  1. customis evaporated under reduced pressure
  2. customleaving a residue which
  3. additionApproximately 10 g of silica gel is mixed with the resulting solution
  4. customThe solvent is evaporated from this mixture
  5. filtrationfilter
  6. washThe silica gel is then eluted with 100 mL of heptane/ethyl acetate (3:1)
  7. customThese solvents are evaporated under reduced pressure
  8. customleaving a residue
  9. additiontreated with 5 g of silica gel
  10. filtrationfiltered
  11. customThe filtrate is evaporated under reduced pressure

Sources & evidence

ORD record
ord-f69b75e593cc4ede95d332bd29d1488a
Source dataset
uspto-grants-1996_03
Patent number
US05502054

Reaction notes

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