37174-96-2

Usage

InChI:InChI=1/C10H18O3/c1-3-5-6-9(11)7-8-10(12)13-4-2/h3-8H2,1-2H3

Upstream product

• 4208-62-2 1-(2-furyl)butan-1-ol 
• 64-17-5 ethanol 
• 14794-31-1 ethyl 3-(chloroformyl)propionate 
• 3431-67-2 di-n-butylcadmium 
• 67404-60-8 C₁₅H₂₈S₅ 
• 110-62-3 pentanal 
• 140-88-5 ethyl acrylate 
• 693-04-9 butyl magnesium bromide 
• 693-03-8 n-butyl magnesium bromide 
• 331991-58-3 ethyl 4-(3,5-dimethylpyrazol-1-yl)-4-oxobutanoate 
• 145653-56-1 ethyl (E)-4-oxo-2-octenoate 

Downstream Products

• 331994-09-3 5-butyl-1-phenyl-1,3-dihydro-pyrrol-2-one 
• 110-15-6 succinic acid 
• 5150-93-6 succinic anhydride monobutyl ester 
• 113330-84-0 5-Butyl-3-[1-phenyl-meth-(E)-ylidene]-3H-thiophen-2-one 
• 90198-91-7 5-butyl-5H-thiophen-2-one 
• 90198-92-8 5-butyl-3H-thiophen-2-one 

Relevant academic research and scientific papers

Preparation of β-substituted γ-keto esters by the grignard reaction on N-acylpyrazoles

Various γ-keto esters were prepared by either the alcoholysis of N-(4-oxoalkanoyl)pyrazoles or the Grignard replacement of pyrazole moiety of 4-(N-pyrazolyl)-4-oxoalkanoic esters. By using 3-phenyl-ι-menthopyrazole as a chiral auxiliary, β-substituted γ-keto esters were enantioselectively obtained.

Reactions of Grignard reagents with bis- or mono-phosphonium ions in Situ generated from Bu3P and dicarboxylic acid dichlorides or ω-ethoxycarbonyl alkanoyl chlorides as a novel method to obtain diketones and ketoesters

Reactions of Grignard reagents with bis-phosphonium or mono-phosphonium ions in situ generated from Bu3P and ClCO(CH2)(n)COCl (5) or ClCO(CH2)(n)CO2Et (13) as a tool for preparation of symmetrical diketones or ketoesters were examined. Addition of Bu3P (2.0 eq) to a THF solution of 5 (n=2) at -40°C followed by addition of n-BuMgCl (2.0 eq) gave the corresponding diketone in good yield. When a mixture of Bu3P and the Grignard reagent (2.0 eq each) was added to the dichloride solution at the same temperature, a better result was obtained. The latter method not with PhMgBr but with n-BuMgCl or MeMgBr was shown to be useful for preparation of symmetrical alkanediones and keto alkanoates from various 5 (n=2 - 6) and 13 (n=2 or 3), respectively. For synthesis of α-diketones or α-ketoesters, only PhMgBr entered the reaction, although the yields were not satisfactory. Addition of a mixture of Bu3P (2.0 eq), MeMgBr (1.0 eq) and BuMgCl (1.0 eq) to a THF solution of 5 (n=4) at -40°C afforded a mixture of 2,7-undecanedione and the corresponding two symmetrical diketones, with the yield of the unsymmetrical diketone being 36%.

Reactions of in situ formed acyl tributylphosphonium ions with Grignard reagents as an effective route to ketones from acid chlorides

The reactions of acyl tributylphosphonium ions in situ generated from acid chlorides and Bu3P in THF at -22°C with primary alkyl and arylmagnesium halides have proved to be a convenient and simple procedure to prepare ketones from acid chloride in one-pot.

Addition of Aldehydes to Activated Double Bonds, XXII. Addition of Aliphatic Aldehydes to α,β-Unsaturated Esters and Nitriles

Thiazolium salt catalysed addition of aliphatic aldehydes to α,β-unsaturated esters and nitriles leads to γ-ketocarboxylic esters (1-24) and γ-ketonitriles (25-32).