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5717-37-3 - (1-Ethoxycarbonylethylidene)triphenylphosphorane, 97% - (1-Carboethoxyethylidene)triphenylphosphorane - Ethyl 2-(triphenylphosphoranylidene)propionate - A15619 - Alfa Aesar

A15619 (1-Ethoxycarbonylethylidene)triphenylphosphorane, 97%

CAS Number
5717-37-3
Synonyms
(1-Carboethoxyethylidene)triphenylphosphorane
Ethyl 2-(triphenylphosphoranylidene)propionate

Size Price ($) Quantity Availability
10g 63.63
25g 141.30
50g 290.46
250g 899.20
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(1-Ethoxycarbonylethylidene)triphenylphosphorane, 97%

MDL
MFCD00009160
EINECS
227-215-4

Chemical Properties

Formula
C23H23O2P
Formula Weight
362.41
Melting point
154-160°
Sensitivity
Air Sensitive
Solubility
Soluble in water.

Applications

(1-Ethoxycarbonylethylidene)triphenylphosphorane is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals. It’s also a Horner-Wadsworth-Emmons reagent. It can be used for olefination. It can also be utilized for the synthesis of more complex compounds, such as (29S,37S)-isomer of malevamide E, a potent ion-channel inhibitor.

Notes

Air sensitive. Avoid contact with oxygen and air. Store away from oxidizing agent. Contains triphenylphosphine oxide.

Literature References

Yasumasa Koyama; Yuichi Fukakusa; Nobuo Kyomura; Saburo Yamagishi; Tadashi Arai. The structure of luteoreticulin, a nitro-containing metabolite of streptomyces luteoreticuli. Tetrahedron Letters. 1969, 10 (5), 355-358.

Vlark F. Beatty; Clive Jennings-White; and Mitchell A. Avery. Stereocontrolled synthesis of (2S,3S,8S,9S,4E,6E)-3-amino-9-methoxy-2,6,8-trimethyl-10-phenyldeca-4,6-dienoic acid (Adda), the amino acid characteristic of microcystins and nodularin. J. Chem. Soc., Perkin Trans. 1. 1992, (13), 1637-1641.

Stable ylide which reacts with aldehydes to give ß-substituted methacrylic esters. See Appendix 1.

With acyl halides, gives allenic esters: Helv. Chim. Acta, 63, 438 (1980); Org. Synth. Coll., 7, 232 (1990):

Reacts with the carbonyl group of succinic anhydride giving an intermediate useful in the synthesis of 2,2-dialkylcyclopentane-1,3-diones: Synthesis, 845 (1986):

Other References

Beilstein
757112
Harmonized Tariff Code
2931.90
TSCA
No

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