(Ethoxycarbonylmethylene)triphenylphosphorane

• Catalog No.: A12896
• CAS Number: 1099-45-2
• M. F.: C22H21O2P
• M. W.: 348.374701
• Purity: 98+%

SYNONYMS

• Title: (乙氧基羰基亚甲基)三苯基磷烷
• IUPAC name: ethyl 2-(triphenyl-λ^5-phosphanylidene)acetate
• IUPAC Traditional name: ethyl 2-(triphenyl-λ^5-phosphanylidene)acetate
• Synonyms: (Carboethoxymethylene)triphenylphosphorane; Ethyl (triphenylphosphoranylidene)acetate

DATABASE IDS

• EC Number: 214-151-7
• CAS Number: 1099-45-2
• Beilstein Number: 754639
• MDL Number: MFCD00009183

PROPERTIES

• Purity: 98+%
• Melting Point: 126-130°C
• Storage Warning: Air Sensitive
• TSCA Listed: 是

REFERENCES

• 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):
  
• 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.
• 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):