119020-91-6

Upstream product

• 119-61-9 benzophenone 
• 5445-17-0 Methyl 2-bromopropionate 
• 17639-93-9 2-chloro-propionic acid methyl ester 
• 76527-25-8 3,3-diphenyloxirane-2-carboxylic acid methyl ester 
• 75-24-1 trimethylaluminum 
• 292638-85-8 acrylic acid methyl ester 

Downstream Products

• 114916-90-4 α-methyl-β,β-diphenyl-methyl propionate 
• 66957-27-5 (C₄H₉)3SnOC(C₆H₅)2CH(CH₃)COOCH₃ 
• 130292-30-7 α-methyl-β,β-diphenylpropionyl chloride 
• 52957-74-1 2-methyl-3-phenyl-1-indanone 
• 5292-20-6 α-methyl-β,β-diphenylpropionic acid 
• 29193-55-3 3,3-diphenyl-3-hydroxy-2-methylpropionic acid 

Relevant academic research and scientific papers

Ni-catalyzed activation of α-chloroesters: a simple method for the synthesis of α-arylesters and β-hydroxyesters

Coupling reactions of α-chloroesters with aryl halides (α-arylation) or carbonyl compounds (Reformatsky) using nickel catalyst allow, under mild conditions, the preparation of various functionalized aryl propionic acid derivatives or β-hydroxyesters. In the synthesis of aryl propionic acid derivatives, the process is efficient with aryl halides bearing either electron-withdrawing or electron-donating groups.

Iron-mediated electrochemical reaction of α-chloroesters with carbonyl compounds

(Matrix presented) Reformatsky-type reactions have been performed efficiently using an electroassisted iron-complex catalysis. Valuable product such as β-hydroxyesters, ketones or nitriles are thus prepared with high yields.

Reductive aldol-type reaction of α,β-unsaturated esters with aldehydes or ketones in the presence of Rh catalyst and Et2Zn

The reaction of RhCl(PPh3)3 with Et2Zn easily generated a rhodium-hydride complex (Rh-H) that added to α,β-unsaturated esters to form rhodium enolate complexes by formal 1,4-reduction. These rhodium enolates gave the corre

Reductive Reformatsky-Honda reaction of α,β-unsaturated esters: Facile formation of 1,3-dicarbonyl compounds and β-hydroxy esters

The reaction of tris(triphenylphosphine)rhodium chloride [RhCl(PPh 3)3] with diethylzinc (Et2Zn) easily afforded a rhodium-hydride complex that effects the 1,4-reduction of α,β- unsaturated esters to give rhodium enolates. Formation of the rhodium enolate is followed by transmetalation with the zinc species to give a Reformatsky-type reagent, and this reacts with various acid chlorides at the α-position to give β-keto esters. The Reformatsky-type reagent also reacts with various electrophiles such as aldehydes, ketones and acid anhydrides to give the corresponding products in which the electrophiles were introduced reductively at the α-position of α,β-unsaturated esters. Copyright

Iron-catalysed Reformatsky-type reactions

A Reformatsky-type reaction has been developed using iron catalysis in acetonitrile or DMF. Reduction of iron(II) bromide by manganese metal in acetonitrile provides a low-valent iron catalyst, which is the active species; under these conditions, α-chloro

Structural similarity and its surprises: Endothelin receptor antagonists -process research and development report

Process research and pilot plant processes are described for three endothelin (ET) receptor antagonists. The efficient synthesis of the parent compound Darusentan proceeds via a Darzens reaction from chloroacetate with benzophenone, addition of methanol to the resulting epoxide, saponification of the alkyl propionate and optical resolution of the racemic acid by crystallisation with a chiral amine. The final stage of the synthetic sequence involves the introduction of a pyrimidine moiety. Intermediates formed during this process can be used as starting materials for the synthesis of the two other ET receptor antagonists BSF 420627 and BSF 302146. An ether exchange reaction, which replaces the methoxy with a phenethyloxy substituent, enabled BSF 420627 to be prepared. The synthetic route to BSF 302146 employs trimethylaluminum to methylate the epoxide produced by the Darzens reaction.

Reformatsky-type addition of esters of α-halogeno carboxylic acids to aldehydes and ketones in the presence of Fe(CO)5

Reformatsky-type addition of esters of α-halogeno carboxylic acids to aldehydes and ketones in the presence of Fe(CO)5 and an activating agent (CBrCl3 or I2) afforded the corresponding esters of β-hydroxy acids in good yields. Possible reaction mechanisms are discussed.

Electrochemical activation of zinc in the coupling reaction of α-bromoesters with carbonyl compounds

The Reformatsky reaction has been examined using a mild and effective method of electrochemical zinc activation, based on the cathodic reduction of a catalytic amount of zing bromide in acetonitrile.

Metal Exchange between an Electrogenerated Organonickel Species and Zinc Halide: Application to an Electrochemical, Nickel-Catalyzed Reformatsky Reaction

The mechanism of the electroreductive coupling of α-chloro esters or α-chloro nitriles with carbonyl compounds by the means of a sacrificial zinc anode and a nickel catalyst was elucidated by electroanalytical techniques.The mechanism involved reduction of a Ni(II) complex to a Ni(0) complex, oxidative addition of the α-chloro ester to the Ni(0) complex, and a Zn(II)/Ni(II) exchange, leading to an organozinc Reformatsky reagent.The electrosynthesis of various β-hydroxy esters, β-hydroxy nitriles, and 2,3-epoxy esters was successfully achieved under extremely mild conditions.

Convenient Synthetic Sequence for the Preparation of Indanones

A convenient and general methods is reported for the synthesis of indanones from aryl ketones or aldehydes.