40309-42-0

Usage

Synthesis Reference(s)

Synthesis, p. 561, 2000 DOI: 10.1055/s-2000-6378

Upstream product

• 141-78-6 ethyl acetate 
• 78-84-2 isobutyraldehyde 
• 34982-24-6 ethyl triphenylstannylacetate 
• 42520-11-6 1,1-diethoxy-2-bromo-ethene 
• 129505-18-6 dimethylsilanyl-acetic acid ethyl ester 
• 105-39-5 chloroacetic acid ethyl ester 
• 623-48-3 ethyl iodoacetae 
• 67-56-1 methanol 
• 7152-15-0 ethyl 4-methyl-3-oxo-pentanoate 
• 105-36-2 ethyl bromoacetate 
• 38491-54-2 ethyl 2-diazo-3-hydroxy-4-methylpentanoate 

Downstream Products

• 89582-40-1 3-hydroxy-4-methylpentanehydrazide 
• 15790-86-0 ethyl-4-methyl-2-(E)-penteneoate 
• 1775-44-6 (2E)-4-methylpent-2-enoic acid 
• 68258-20-8 2-(2,2-dimethylcyclopropyl)acetic acid 

Relevant academic research and scientific papers

Reduction of aromatic and aliphatic keto esters using sodium borohydride/MeOH at room temperature: a thorough investigation

Reduction of keto esters is a valuable alternative to produce diols. Sodium borohydride/MeOH system at room temperature and short reaction time efficiently reduced α, β, γ, and δ-keto esters having α-keto esters as the most reactive. The ester functionality was reduced effectively due to the presence of oxo group that somehow facilitates the formation of ring intermediate. As expected, the chemoselective experiments showed that ester functionality was not reduced using this system. This study presents a simple, easy, and benign reduction process of various keto esters to its corresponding diols.

A simple and efficient procedure of low valent iron- or copper-mediated reformatsky reaction of aldehydes

(Chemical Equation Presented) An operationally simple and very efficient procedure of Reformatsky reaction of aldehydes has been carried out in THF in the presence of low valent iron or copper which were prepared in situ employing a bimetal redox strategy through reduction of FeCl3 or CuCl 2-2H2O with magnesium.

Stereoselective enzymatic synthesis of chiral alcohols with the use of a carbonyl reductase from Candida magnoliae with anti-prelog enantioselectivity

In our effort to search for carbonyl reductases with anti-Prelog enantioselectivity, the activity and enantioselectivity of a carbonyl reductase from Candida magnoliae have been examined with various ketones of diverse structures. This carbonyl reductase catalyzed the reduction of a series of ketones, α-and β-ketoesters, to anti-Prelog configurated alcohols in excellent optical purity. The usefulness of this carbonyl reductase has been demonstrated by synthesis of several chiral alcohol intermediates of pharmaceutical importance.

Synthesis of isotetronic acids by cyclization of 1,3-bis(trimethylsilyloxy) alk-1-enes with oxalyl chloride

Isotetronic acids were regioselectively prepared by cyclization of 1,3-bis(trimethylsilyloxy)alk-1-enes with oxalyl chloride.

Metal chloride-promoted aldol reaction of α-dimethylsilylesters with aldehydes, ketones, and α-enones

In the presence of a catalytic amount of LiCl, α-dimethylsilylesters (α-DMS-esters) 1 smoothly reacted with various aldehydes at 30°C to give aldols in good to high yields. On the other hand, the aldol reaction with ketones was effectively promoted by MgCl2 rather than by LiCl. α-Enones also underwent the metal chloride-promoted addition of 1 at the carbonyl carbon or β-carbon. Georg Thieme Verlag Stuttgart.

Titanocene(III)-promoted Reformatsky additions

(Equation presented) A novel method for the promotion of Reformatsky-like reactions is presented. The technique employs titanocene(III) chloride as a mild and homogeneous single-electron reductant. The reactions are rapid, operationally simple, and compatible with a wide range of functionalities. These additions are also anti diastereoselective.

Ultrasound promoted synthesis of β-hydroxyesters by reformatsky reaction using indium metal

Ultrasound promoted Reformatsky reaction by the reaction of aldehydes or ketone with ethyl bromoacetate in the presence of indium metal afforded β-hydroxyesters in good to excellent yields under mild conditions.

A practical method for the Reformatsky reaction of aldehydes

Reformaksky reaction of aliphatic aldehydes has been performed successfully by the addition of BF3·OEt2 to a stirred suspension of aldehyde, bromo ester and Zn dust in aqueous THF. For aromatic aldehydes, addition of benzoyl peroxide is also required to effect the reaction.

A mild method for protodesilylation of α-dimethylphenylsilyl ester substrates

Mild conditions (1.2 eq. Hg(OAc)2, 1.2 eq. TBAF in 1:1 MeOH/THF; 35 min at 0 °C) have been developed for the protodesilylation of α- dimethylphenylsilyl esters. An enolate-dependent mechanism for the reaction was supported through studies indicating the clean incorporation of deuterium. To further investigate the mechanism, the optimal conditions as well as the kinetics of the reaction were explored.