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420670 Sigma-Aldrich

Ethyl 3-oxo-4-(triphenylphosphoranylidene)butyrate

97%

Synonym: 3-Oxo-4-(triphenylphosphoranylidene)butanoic acid ethyl ester, 4-(Triphenylphosphoranylidene)acetoacetic acid ethyl ester, [3-(Ethoxycarbonyl)-2-oxopropylidene]triphenylphosphorane

  • CAS Number 13148-05-5

  • Linear Formula (C6H5)3P=CHCOCH2CO2C2H5

  • Molecular Weight 390.41

  •  MDL number MFCD00192162

  •  PubChem Substance ID 24866344

  •  NACRES NA.22

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Properties

Related Categories C-C Bond Formation, Chemical Synthesis, Olefination, Synthetic Reagents, Wittig Reagents More...
Quality Level   100
assay   97%
reaction suitability   reaction type: C-C Bond Formation
storage temp.   room temp
SMILES string   CCOC(=O)CC(=O)C=P(c1ccccc1)(c2ccccc2)c3ccccc3
InChI   1S/C24H23O3P/c1-2-27-24(26)18-20(25)19-28(21-12-6-3-7-13-21,22-14-8-4-9-15-22)23-16-10-5-11-17-23/h3-17,19H,2,18H2,1H3
InChI key   QYXSFVCJCUXGJH-UHFFFAOYSA-N

Description

Application

Can be coupled with glyoxals in a one-step route to 4-hydroxycyclopentanones. Also used to prepare 2H-pyran-2-ones from oxazolones.

Reactant for stereoselective synthesis of:
• Polysubstituted cyclopentanones via double Michael addition reactions
• Hydroindanes via asymmetric quadruple aminocatalytic three-component domino condensation and spirocyclization
• Oxocyclohexenecarboxylates by cyclocondensation

Reactant for preparation of:
• γ-(Dioxobutylidene)butenolides
• Chain conjugated 2H-pyran-5-carboxylates
• 2-Substituted pyridoacridines with antitumor activity by means of thermolysis

Packaging

5 g in glass bottle

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable
Protocols & Articles
Peer-Reviewed Papers
15

References

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