97139-82-7

Usage

Preparation

Obtained by reaction of acetic anhydride with 2-hydroxypropiophenoneAlso obtained by reaction of ethylmagnesium bromide with 2-acetoxybenzoyl chloride (84%).

InChI:InChI=1/C11H12O3/c1-3-10(13)9-6-4-5-7-11(9)14-8(2)12/h4-7H,3H2,1-2H3

Upstream product

• 610-99-1 1-(2-Hydroxy-phenyl)-propan-1-on 
• 108-24-7 acetic anhydride 
• 925-90-6 ethylmagnesium bromide 
• 5538-51-2 O-acetylsalicyloyl chloride 
• 19311-91-2 N,N-diethylsalicylamide 
• 1441-87-8 salicyloyl chloride 
• 41390-40-3 2-[(cyclohexylamino)carbonyl]phenyl acetate 
• 557-20-0 diethylzinc 

Downstream Products

• 1846-74-8 3-benzoyl-chromen-2-one 
• 1539292-97-1 C₄₀H₃₀O₁₃ 
• 1539293-01-0 C₄₂H₃₄O₁₄ 
• 1539293-02-1 C₂₀H₁₆O₆ 
• 1539293-04-3 C₃₀H₃₆O₆ 
• 64267-12-5 7-(methyloxy)-3-(phenylcarbonyl)-2H-chromen-2-one 
• 19088-67-6 7-hydroxy-3-(phenylcarbonyl)-2H-chromen-2-one 
• 35115-14-1 1-(o-hydroxyphenyl)-2-methylbutane-1,3-dione 

Relevant academic research and scientific papers

Chemoselective synthesis of ketones and ketimines by addition of organometallic reagents to secondary amides

The development of efficient and selective transformations is crucial in synthetic chemistry as it opens new possibilities in the total synthesis of complex molecules. Applying such reactions to the synthesis of ketones is of great importance, as this motif serves as a synthetic handle for the elaboration of numerous organic functionalities. In this context, we report a general and chemoselective method based on an activation/addition sequence on secondary amides allowing the controlled isolation of structurally diverse ketones and ketimines. The generation of a highly electrophilic imidoyl triflate intermediate was found to be pivotal in the observed exceptional functional group tolerance, allowing the facile addition of readily available Grignard and diorganozinc reagents to amides, and avoiding commonly observed over-addition or reduction side reactions. The methodology has been applied to the formal synthesis of analogues of the antineoplastic agent Bexarotene and to the rapid and efficient synthesis of unsymmetrical diketones in a one-pot procedure. Macmillan Publishers Limited. All rights reserved.

Addition of Grignard reagents to aryl acid chlorides: An efficient synthesis of aryl ketones

(Chemical Equation Presented) Direct addition of Grignard reagents to acid chlorides in the presence of bis[2-(N,N-dimethylamino)ethyl] ether proceeds selectively to provide aryl ketones in high yields. A possible tridentate interaction between Grignard reagents and bis[2-(N,N-dimethylamino)ethyl] ether moderates the reactivity of Grignard reagents, preventing the newly formed ketones from nucleophilic addition by Grignard reagents.