22406-80-0

Upstream product

• 930-68-7 cyclohexenone 
• 141-78-6 ethyl acetate 
• 105-39-5 chloroacetic acid ethyl ester 
• 105-36-2 ethyl bromoacetate 
• 42520-11-6 1,1-diethoxy-2-bromo-ethene 

Downstream Products

• 65093-64-3 ethyl 2-(3-oxocyclohex-1-en-1-yl)acetate 

Relevant academic research and scientific papers

PROCESS FOR PRODUCING FUSED IMIDAZOLE COMPOUND, REFORMATSKY REAGENT IN STABLE FORM, AND PROCESS FOR PRODUCING THE SAME

The present invention provides an industrially advantageous process for producing a steroid C17,20 lyase inhibitor represented by the general formula (I): and a Reformatsky reagent in a stable form suitable for the process.In the present invention, a compound represented by the general formula (I) is produced by reducing a specific β-hydroxy ester compound derivative or a salt thereof obtained from a specific carbonyl compound in a Reformatsky reaction in the presence of a metal hydride complex and a metal halide, and then subjecting it to a ring-closing reaction. In the above Reformatsky reaction, it is useful to use a stable solution of a compound represented by the general formula BrZnCH2COOC2H5 or a crystal of the compound which is represented by the formula (BrZnCH2COOC2H5·THF)2.

Rhodium-catalyzed reformatsky-type reaction

(equation presented) A novel Reformatsky-type reaction was developed using RhCl(PPh3)3 and diethylzinc. Inter- and intramolecular Reformatsky-type reactions were achieved efficiently under mild reaction conditions to give β-hydroxy esters.

Obtention of 2,2-(diethoxy) vinyl lithium and 2-methyl-4-ethoxy butadienyl lithium by Arene-catalysed lithiation of the corresponding chloro derivatives. Synthetic applications

Vinylic lithium reagents 1 and 2 could be obtained by the title procedure from their chloro precursors 5 and 6 instead of the less stable corresponding bromo derivatives 3 and 4. Condensation with carbonyl compounds leads to interesting synthetic applications such as a two steps synthesis of retinal 13 from β-cyclocitral 10.

2,2-Di(ethoxy)vinyllithium: Reactions with carbonyl compounds

2,2-Di(ethoxy)vinyllithium 2 generated from bromo ketene acetal 1 reacts with carbonyl compounds to give either β-hydroxy esters 5 or conjugated esters 6 or hydroxy ketene acetals 7 according to the work up.

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.

Efficient addition of cerium(III) enolate of ethyl acetate to ketones: application to the synthesis of β-ethoxycarbonylmethyl α,β-unsaturated ketones

The cerium(III) enolate derived from ethyl acetate was shown to undergo facile addition with ketones.With conjugated enones, 1,2-addition products were formed exclusively.Oxidative 1,3-oxygen transportation of these products provides an efficient route to