82495-75-8 Usage
Uses
Used in Organic Chemistry:
2-(TRIMETHYLSILYL)ETHOXYMETHYLTRIPHENYLPHOSPHONIUM CHLORIDE is used as a reagent for the synthesis of enol ethers from aldehydes and ketones, which are important intermediates in organic chemistry.
Used in Pharmaceutical Industry:
2-(TRIMETHYLSILYL)ETHOXYMETHYLTRIPHENYLPHOSPHONIUM CHLORIDE is used as a reagent in the preparation of Benzodecalindiones, which are antitumor agents. Its application in this field contributes to the development of potential cancer treatments.
Preparation
Involves reaction of triphenylphosphine
with 2-(trimethylsilyl)ethoxymethyl chloride in benzene at gentle
reflux for 18 h. Upon cooling, the resulting phosphonium salt
can be recovered by filtration and purified by triturating with
diethyl ether in 94% yield.
Purification Methods
Wash the solid with AcOH and recrystallise it from CH2Cl2/EtOAc. Dry it in a vacuum desiccator. Hygroscopic. 1H NMR (CDCl3) : -0.2 (s, Me3Si), 0.8 (t, 8Hz, CH2Si), 3.83 (t, 8Hz, OCH2), 5.77 (d, JPH 4Hz, P+-CH2O) and 7.70 (m, aromatic H). [Sch.nauer & Zbiral Justus Liebigs Ann Chem 1039 1983.]
Check Digit Verification of cas no
The CAS Registry Mumber 82495-75-8 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,2,4,9 and 5 respectively; the second part has 2 digits, 7 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 82495-75:
(7*8)+(6*2)+(5*4)+(4*9)+(3*5)+(2*7)+(1*5)=158
158 % 10 = 8
So 82495-75-8 is a valid CAS Registry Number.
InChI:InChI=1/C24H30OPSi.ClH/c1-27(2,3)20-19-25-21-26(22-13-7-4-8-14-22,23-15-9-5-10-16-23)24-17-11-6-12-18-24;/h4-18H,19-21H2,1-3H3;1H/q+1;/p-1
82495-75-8Relevant academic research and scientific papers
Intramolecular Diels-Alder Cycloaddition Approach toward the cis-Fused Δ5,6-Hexahydroisoindol-1-one Core of Cytochalasins
Xu, Jingjing,Lin, Benguo,Jiang, Xiuqing,Jia, Zejun,Wu, Jinlong,Dai, Wei-Min
supporting information, p. 830 - 834 (2019/01/26)
Synthesis of the cis-fused Δ5,6-hexahydroisoindol-1-one core of cytochalasins B2-B5, K, Z8, Z9, Z12-Z15, and Z17 has been established starting from an intramolecular D
REACTIONS WITH ORGANOPHOSPHORUS COMPOUNDS, 50. TRIMETHYLSILYLETHOXYMETHYLENE TRIPHENYLPHOSPHORANE, A NOVEL REAGENT FOR THE HOMOLOGATION OF CARBONYL COMPOUNDS.
Schoenauer, K.,Zbiral, E.
, p. 573 - 576 (2007/10/02)
Homologation of aldehydes and ketones is achieved by means of trimethylsilylethoxymethylene triphenylphosphorane.
