methyl 5-(1-acetoxy-2-methoxycarbonylallyl)-3-phenylisoxazole-4-carboxylate

Base Information

• Chemical Name: methyl 5-(1-acetoxy-2-methoxycarbonylallyl)-3-phenylisoxazole-4-carboxylate
• CAS No.: 811446-66-9
• Molecular Formula: C₁₈H₁₇NO₇
• Molecular Weight: 359.335

Synonyms:methyl 5-(1-acetoxy-2-methoxycarbonylallyl)-3-phenylisoxazole-4-carboxylate

Chemical Property of methyl 5-(1-acetoxy-2-methoxycarbonylallyl)-3-phenylisoxazole-4-carboxylate

Chemical Property:

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Technology Process of methyl 5-(1-acetoxy-2-methoxycarbonylallyl)-3-phenylisoxazole-4-carboxylate

There total 2 articles about methyl 5-(1-acetoxy-2-methoxycarbonylallyl)-3-phenylisoxazole-4-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.0%

acetyl chloride (75-36-5) + methyl 5-(1-hydroxy-2-methoxycarbonylallyl)-3-phenylisoxazole-4-carboxylate (811446-54-5) → methyl 5-(1-acetoxy-2-methoxycarbonylallyl)-3-phenylisoxazole-4-carboxylate (811446-66-9)

Guidance literature:

With pyridine; In dichloromethane; at 0 ℃; for 0.0833333h;

DOI:10.1055/s-2004-831179

Reference yield:

5-formyl-3-phenyl-isoxazole-4-carboxylic acid methyl ester (161126-45-0) → methyl 5-(1-acetoxy-2-methoxycarbonylallyl)-3-phenylisoxazole-4-carboxylate (811446-66-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / DABCO / tetrahydrofuran / 0.08 h / 20 °C

2: 88 percent / pyridine / CH₂Cl₂ / 0.08 h / 0 °C

With pyridine; 1,4-diaza-bicyclo[2.2.2]octane; In tetrahydrofuran; dichloromethane; 1: Baylis-Hillman reaction;

DOI:10.1055/s-2004-831179

Reference yield: 63.0%

benzylamine (100-46-9) + methyl 5-(1-acetoxy-2-methoxycarbonylallyl)-3-phenylisoxazole-4-carboxylate (811446-66-9) → methyl 5-benzyl-4-oxo-3-phenyl-5,6-dihydro-4H-isoxazolo[4,5-c]azepine-7-carboxylate + methyl 5-(3-benzylamino-2-methoxycarbonylpropenyl)-3-phenylisoxazole-4-carboxylate

Guidance literature:

In methanol; at 20 ℃;

DOI:10.1055/s-2004-831179

upstream raw materials:

acetyl chloride

methyl 5-(1-hydroxy-2-methoxycarbonylallyl)-3-phenylisoxazole-4-carboxylate

5-formyl-3-phenyl-isoxazole-4-carboxylic acid methyl ester

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