27349-40-2 | 5-Isoxazoleaceticacid,3-methyl-,methylester(8CI,9CI)

Packsize	Purity	Availability	Price	Discounted Price
100mg	98%	in stock	$20.00	$14.00
250mg	98%	in stock	$43.00	$31.00

Description

• Catalog Number: AF53105
• Chemical Name: 5-Isoxazoleaceticacid,3-methyl-,methylester(8CI,9CI)
• CAS Number: 27349-40-2
• Molecular Formula: C7H9NO3
• Molecular Weight: 155.15125999999998
• MDL Number: MFCD18833104
• SMILES: COC(=O)Cc1onc(c1)C

Upstream Synthesis Route

To synthesize 5-Isoxazoleacetic acid, 3-methyl-, methyl ester (8CI,9CI), several steps are required. This compound is also known as methyl 5-methylisoxazole-3-acetate. The synthesis can be approached by constructing the isoxazole ring and subsequently esterifying the carboxylic group. Here is a concise route:

1. Start with the preparation of the appropriate oxime. This can be achieved by reacting propanone (acetone) with hydroxylamine under acidic conditions to form acetone oxime.

2. Oxime undergoes cyclization with a β-halopropionic acid such as β-chloropropionic acid. This step is carried out under reflux with a base such as sodium hydroxide to facilitate the formation of the isoxazole ring. This yields 3-methyl-5-hydroxyisoxazole.

3. Perform oxidation of the 5-hydroxyisoxazole using an oxidizing agent, such as Jones reagent (chromium trioxide in sulfuric acid), to convert the alcohol to the carboxylic acid, resulting in 5-isoxazoleacetic acid, 3-methyl-.

4. Esterify the carboxylic group using methanol in the presence of a strong acid catalyst like sulfuric acid or an acid chloride method to form the target compound, 5-Isoxazoleacetic acid, 3-methyl-, methyl ester. This can also be achieved using diazomethane, which is especially handy for forming methyl esters.

This synthesis route assumes access to standard laboratory equipment and expertise in handling potentially hazardous reagents.