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1099-45-2 - (Ethoxycarbonylmethylene)triphenylphosphorane, 98+% - (Carboethoxymethylene)triphenylphosphorane - Ethyl (triphenylphosphoranylidene)acetate - A12896 - Alfa Aesar

A12896 (Ethoxycarbonylmethylene)triphenylphosphorane, 98+%

CAS-Nummer
1099-45-2
Synonyme
(Carboethoxymethylene)triphenylphosphorane
Ethyl (triphenylphosphoranylidene)acetate

Größe Preis ($) Menge Verfügbarkeit
10g 24,90
50g 98,60
250g 403,00
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(Ethoxycarbonylmethylene)triphenylphosphorane, 98+%

MDL
MFCD00009183
EINECS
214-151-7

Chemische Eigenschaften

Formel
CH3CH2O2CCH=P(C6H5)3
Molmasse
348.38
Schmelzpunkt
126-130°
Sensitivität
Air Sensitive
Löslichkeit
Soluble in organic solvents. Insoluble in water.

Anwendungen

(Ethoxycarbonylmethylene)triphenylphosphoran is used as a Wittig reagent in organic synthesis. It is used in the preparation of indole from o-nitrobenzaldehydes, coumarins from o-hydroxy acetophenone. It acts as an inhibitor and inhibits the activity of cholinesterase.

Bemerkungen

Air sensitive. Keep the container tightly closed in a dry and well-ventilated place. Incompatible with strong oxidizing agents.

Literaturverweise

Stable crystalline ylide which reacts with aldehydes giving substituted ethyl acrylates. This reaction has been used in an indole synthesis from o-nitrobenzaldehydes: Synthesis, 862 (1984); 401 (1987):

Coumarins have been synthesized from o-hydroxy acetophenones: Monatsh. Chem., 115, 765 (1984); o-hydroxy aldehydes give the 4-unsubstituted analogues: Chem. Pharm. Bull., 39, 3100 (1991); 42, 2032 (1994); Indian J. Chem. B, 32, 1159 (1993):

More highly-substituted ylides can be prepared by alkylation (e.g. with benzyl bromide) and abstraction of a proton by NaOH. See, e.g.: Synth. Commun., 19, 1899 (1989).

Reaction with acid chlorides leads to esters of allenic acids. See, e.g.: Org. Synth. Coll., 7, 232 (1990).

See also (Methoxycarbonyl­methyl­ene)­triphenyl­phosphorane, A14020, and Appendix 1.

/n

Bujaranipalli, S.; Das, S. Synthesis of (3R,5S)-5-hydroxy-de-O-methyllasiodiplodin: a facile and stereoselective approach. Tetrahedron Lett. 2015, 56 (24), 3747-3749.

Nagaraju, K.; Mainkar, P. S.; Chandrasekhar, S. Convergent synthesis of fully functionalized decalin skeleton of (+)-fusarisetin A. Tetrahedron Lett. 2015, 56 (2), 404-405.

Weitere Referenzen

Beilstein
754639
Harmonized Tariff Code
2931.90
TSCA
Yes

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