69083-54-1

Upstream product

• 17448-81-6 ethyl 2-acetyl-3-oxopentanoate 
• 2510-36-3 3,5-dimethyl-4-isoxazolecarboxylic acid 
• 74-88-4 methyl iodide 
• 93599-39-4 4-(4,4-Dimethyl-4,5-dihydro-oxazol-2-yl)-5-ethyl-3-methyl-isoxazole 
• 99298-88-1 N-(2-hydroxyl-1,1-dimethylethyl) 3,5-dimethyl-isoxazole-3-carboxamide 
• 93599-35-0 4-(4',5'-dihydro-4',4'-dimethyl-Δ²-oxazolin-2-yl)-3,5-dimethylisoxazole 
• 31301-45-8 3,5-dimethylisoxazole-4-carbonyl chloride 

Downstream Products

• 90087-36-8 3-methyl-5-isopropyl-4-isoxazolecarboxylic acid 
• 87967-94-0 5-Ethyl-3-methyl-isoxazole-4-carbaldehyde 
• 144272-67-3 3-methyl-5-((R,S)-1'-(phenylthio)-1'-ethyl)-4-<<(S)-2'-(hydroxymethyl)-N-pyrrolidino>carbonyl>isoxazole 

Relevant academic research and scientific papers

Metalation of Isoxazolyloxazolines, a Facile Route to Functionally Complex Isoxazoles: Utility, Scope, and Comparison to Dianion Methodology

2-(5'-Alkylisoxazol-4'-yl)-Δ2-oxazoline was metalated at the C-5' alkyl group, and the lithio anion was quenched with a variety of electrophiles.Alkyl halides, aldehydes, and acylpyridinium salts were used as electrophiles.The lithio anion was oxygenated with MOOPH or N-(phenylsulfonyl)oxaziridene.The isoxazolyloxazoline system was converted to the isoxazolyl carboxylic acid, aldehyde, ketone, and chiral oxazoline.The isoxazolyloxazoline was formed, metalated, and deprotected in synthetically useful yields and represents a facile entry into functionally complex isoxazoles.To determine the necessity of the oxazoline protection/deprotection scheme, dianions of isoxazole-4-carboxylic acids were studied.The dianion method was found to be more efficient for simple alkyl halides, but limited in scope.

A FACILE SYNTHESIS OF FUNCTIONALLY COMPLEX ISOXAZOLE DERIVATIVES

Metalation of 2(4'-Isoxazolyl)-Δ2-oxazolines takes place initially and selectively on the C-5'-alkyl group.Subsequent metalation also proceeds at this position.Selective deprotection of the oxazoline was accomplished without disturbing the izox