475562-17-5

Basic information

• Product Name: methyl (4E)-5-chloro-2-(1-methylethyl)pent-4-enoate
• Synonyms: 4-pentenoic acid, 5-chloro-2-(1-methylethyl)-, methyl ester, (4E)-; Methyl (4E)-5-chloro-2-isopropylpent-4-enoate
• CAS NO: 475562-17-5
• Molecular Formula: C₉H₁₅ClO₂
• Molecular Weight: 190.6672
• Mol File: 475562-17-5.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 203.255°C at 760 mmHg
• Flash Point: 76.725°C
• Density: 1.023g/cm³
• Vapor Pressure: 0.28mmHg at 25°C
• Refractive Index: 1.453
• CAS DataBase Reference: methyl (4E)-5-chloro-2-(1-methylethyl)pent-4-enoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (4E)-5-chloro-2-(1-methylethyl)pent-4-enoate(475562-17-5)
• EPA Substance Registry System: methyl (4E)-5-chloro-2-(1-methylethyl)pent-4-enoate(475562-17-5)

Safety Data

• Hazardous Substances Data: 475562-17-5(Hazardous Substances Data)

Upstream product

• 51122-91-9 dimethyl isopropylmalonate 
• 72651-95-7 5-isopropyl-2,2-dimethyl-[1,3]dioxane-4,6-dione 
• 1358791-91-9 5-(3-chloro-allyl)-5-isopropyl-2,2-dimethyl-[1,3]dioxane-4,6-dione 
• 124-41-4 sodium methylate 
• 10061-02-6 (E)-1,3-dichloro-prop-1-ene 
• 705259-97-8 dimethyl 2-[(2E)-3-chloro-2-propenyl]-2-isopropyl malonate 
• 67-56-1 methanol 
• 87953-16-0 (4E)-5-chloro-2-isopropyl-4-pentenoic acid 

Downstream Products

• 387353-77-7 methyl (S)-(4E)-5-chloro-2-isopropyl-4-pentenoate 
• 883229-15-0 (R)-(4E)-5-chloro-2-isopropyl-4-pentenoic acid 
• 87953-16-0 (4E)-5-chloro-2-isopropyl-4-pentenoic acid 
• 324519-68-8 trans-(2S)-5-chloro-2-isopropyl-N,N-dimethyl-4-pentenamide 

Relevant articles and documents

PROCESS FOR PREPARING ALISKIREN AND ITS INTERMEDIATES

The present application relates to a process for the preparation of aliskiren and its pharmaceutically acceptable salts. In particular, the present application relates to a process for the preparation of intermediates for aliskiren, and their conversion to aliskiren or its salts.

PROCESS FOR PREPARING RACEMIC ALKYL-5-HALOPENT-4-ENECARBOXYLIC ACIDS OR -CARBOXYLIC ESTERS

A process for preparing racemic alkyl-5-halopent-4-enecarboxylic acids and esters thereof of the formula (I), in which R is a C1-C6-alkyl radical, R1 is H or C1-4-alkyl and X is chlorine, bromine or iodine, which comprises a) reacting a dialkyl alkylmalonate of the formula (II),in which R is as defined above and R2 is a C1-C4-alkyl radical, in the presence of a metal alkoxide of the formula MOR3, in which M may be Na, K or Li, and R3 is a C1-C4-alkyl radical, and in an organic solvent, with 1,3-dihalopropene to give the corresponding allylated malonate, then b) after full conversion, adding an inorganic salt and a C1-C6 alcohol to the reaction mixture, heating the reaction mixture to reflux temperature, then c) isolating the desired racemic ester of the formula (I) from the reaction mixture by extraction or direct distillation and d) if the racemic acid is the desired end product, hydrolyzing the ester function.

PROCESSES FOR PRODUCING (4E)-5-CHLORO-2-ISOPROPYL-4-PENTENOIC ESTER AND OPTICALLY ACTIVE ISOMER THEREOF

The present invention provides processes for producing a (4E)-5-chloro-2-isopropyl-4-pentenoate and an optical isomer of the (4E)-5-chloro-2-isopropyl-4-pentenoate, namely a process for producing a (4E)-5-chloro-2-isopropyl-4-pentenoate represented by the following formula (4), which comprises reacting a compound represented by the following formula (2) in the presence of an aprotic solvent (II) with a base (II) and then with (1E)-1,3-dichloro-1-propene to give a compound represented by the following formula (3), and dealkoxycarbonylating either ester in the compound represented by the following formula (3), and a process for producing a (S)-(4E)-5-chloro-2-isopropyl-4-pentenoate represented by the following formula (5), which comprises optically resolving a (4E)-5-chloro-2-isopropyl-4-pentenoate represented by the formula (4) obtained by the above-mentioned process (wherein R is a lower alkyl group or an aralkyl group).