5717-37-3 Usage
Description
Ethyl 2-(triphenylphosphoranylidene)propionate, also known as (1-Ethoxycarbonylethylidene)triphenylphosphorane, is a yellow crystalline powder with significant applications in various fields. It is an important raw material and intermediate used in organic synthesis, pharmaceuticals, and agrochemicals. Its unique chemical structure allows it to act as a Horner-Wadsworth-Emmons reagent, which is crucial for olefination reactions and the synthesis of more complex compounds.
Uses
Used in Organic Synthesis:
Ethyl 2-(triphenylphosphoranylidene)propionate is used as a key intermediate for the synthesis of various organic compounds. Its ability to act as a Horner-Wadsworth-Emmons reagent makes it a valuable tool in the creation of new molecules with potential applications in various industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Ethyl 2-(triphenylphosphoranylidene)propionate is used as a crucial component in the development of new drugs. Its role in olefination reactions and the synthesis of complex compounds contributes to the discovery and production of innovative medications.
Used in Agrochemical Industry:
Ethyl 2-(triphenylphosphoranylidene)propionate is also utilized in the agrochemical industry for the synthesis of various agrochemical products. Its versatility as a reagent and intermediate allows for the development of new compounds with potential applications in agriculture, such as pesticides and fertilizers.
Used in Synthesis of Complex Compounds:
Ethyl 2-(triphenylphosphoranylidene)propionate is used as a reagent for the synthesis of more complex compounds, such as (29S,37S)-isomer of malevamide E, a potent ion-channel inhibitor. This application highlights its importance in the development of new and effective therapeutic agents.
Synthesis
Ethyl 2-(triphenylphosphoranylidene)propionate was prepared this reagent from ethyl 2-bromopropanoate and triphenylphosphine.A 500-mL, one-necked, round-bottomed flask equipped with an egg-shaped magnetic stirring bar is charged with triphenylphosphine (52.46 g, 200.0 mmol), ethyl acetate (130 mL), and ethyl 2-bromopropanoate (26.03 mL, 200.0 mmol). A reflux condenser is attached to the flask and the solution is heated under reflux (oil bath temperature: 75-80 °C) under argon for 24 h. The resulting white precipitate is collected through suction filtration on a Büchner funnel and washed with ethyl acetate (100 mL). The salt is dissolved in dichloromethane (500 mL) and the solution is transferred to a 1-L separation funnel. Aqueous sodium hydroxide solution (2 M, 200 mL) is added and, after vigorously shaking, the organic and aqueous layers are separated. The aqueous phase is extracted with dichloromethane (100 mL). The combined organic phases are washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated at 30 °C under rotary evaporation (20-25 mmHg); drying under vacuum (0.1-0.2 mmHg) affords 54.51 g (75.2%) of ethyl 2-(triphenylphosphoranylidene)propionate as a light-yellow solid, mp 156-158 °C.
Check Digit Verification of cas no
The CAS Registry Mumber 5717-37-3 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,7,1 and 7 respectively; the second part has 2 digits, 3 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 5717-37:
(6*5)+(5*7)+(4*1)+(3*7)+(2*3)+(1*7)=103
103 % 10 = 3
So 5717-37-3 is a valid CAS Registry Number.
InChI:InChI=1/C29H27NO4/c1-19-14-20(2)16-24(15-19)30-21(3)27(29(32)33-4)28(31)26(30)17-22-10-12-25(13-11-22)34-18-23-8-6-5-7-9-23/h5-17H,18H2,1-4H3/b26-17+
