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Ethyl 3-oxo-4-(triphenylphosphoranylidene)butyrate

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Ethyl 3-oxo-4-(triphenylphosphoranylidene)butyrate Basic information
Product Name:Ethyl 3-oxo-4-(triphenylphosphoranylidene)butyrate
Synonyms:[3-(Ethoxycarbonyl)-2-oxopropylidene]triphenylphosphorane, 98 %;[3-(ETHOXYCARBONYL)-2-OXOPROPYLIDENE]TRIPHENYLPHOSPHORANE;Ethyl 3-oxo-4-(triphenylphosphoranylidene)butanoate;Ethyl 3-oxo-4-(triphenylphosphoranylidene)butyrate, [3-(Ethoxycarbonyl)-2-oxopropylidene]triphenylphosphorane;3-Oxo-4-(triphenylphosphoranylidene)butanoic Acid Ethyl Ester;4-(Triphenylphosphoranylidene)acetoacetic Acid Ethyl Ester;Ethyl 3-oxo-4-(triphenylphosphoranylidene)butyrate,97%;Butanoic acid, 3-oxo-4-(triphenylphosphoranylidene)-, ethyl ester
CAS:13148-05-5
MF:C24H23O3P
MW:390.41
EINECS:
Product Categories:Wittig Reagents;Miscellaneous Reagents;C-C Bond Formation;Olefination
Mol File:13148-05-5.mol
Ethyl 3-oxo-4-(triphenylphosphoranylidene)butyrate Structure
Ethyl 3-oxo-4-(triphenylphosphoranylidene)butyrate Chemical Properties
Melting point 101-106 °C
Boiling point 544.0±52.0 °C(Predicted)
density 1.18±0.1 g/cm3(Predicted)
storage temp. -20°C Freezer
solubility Acetone, Dichloromethane, Methanol
form solid
color Off-White to Pale Yellow
Stability:Moisture Sensitive
InChI1S/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
InChIKeyQYXSFVCJCUXGJH-UHFFFAOYSA-N
SMILESCCOC(=O)CC(=O)C=P(c1ccccc1)(c2ccccc2)c3ccccc3
Safety Information
Safety Statements 24/25
WGK Germany 3
HS Code 29319090
Storage Class11 - Combustible Solids
MSDS Information
ProviderLanguage
SigmaAldrich English
ACROS English
Ethyl 3-oxo-4-(triphenylphosphoranylidene)butyrate Usage And Synthesis
DescriptionEthyl 3-oxo-4-(triphenylphosphoranylidene)butyrate is a Wittig reagent for the stereoselective synthesis of (Z)-enones; annulation reagent for the synthesis of cyclohexenones.
Chemical PropertiesOff-White Powder
UsesEthyl 3-oxo-4-(triphenylphosphoranylidene)butyrate can be a useful synthetic intermediate in the production of antibiotics.
UsesCan be coupled with glyoxals in a one-step route to 4-hydroxycyclopentanones. Also used to prepare 2H-pyran-2-ones from oxazolones.
reaction suitabilityreaction type: C-C Bond Formation
SynthesisEthyl 4- (Triphenylphosphoranylidene)acetoacetate is prepared in two steps from ethyl or methyl 4-chloroacetoacetates (see Ethyl 4-Chloroacetoacetate), respectively, in 58-68% overall yield (eq 1).
Tag:Ethyl 3-oxo-4-(triphenylphosphoranylidene)butyrate(13148-05-5) Related Product Information
Ethyl 3-oxo-4-(triphenylphosphoranylidene)butyrate 1-(Triphenyl-lambda5-phosphanylidene)-butan-2-one (Acetylmethylene)triphenylphosphorane (Formylmethylene)triphenylphosphorane [2-(Ethoxycarbonyl)-2-oxoethylidene]triphenylphosphorane Ethyl (triphenylphosphoranylidene)acetate