3-trimethylmethylcarbonyl-6-{(E)-[2-(4-methoxycarbonyl)phenyl]ethenyl}pyridoxal monomethyl acetal

Base Information

• Chemical Name: 3-trimethylmethylcarbonyl-6-{(E)-[2-(4-methoxycarbonyl)phenyl]ethenyl}pyridoxal monomethyl acetal
• CAS No.: 258531-75-8
• Molecular Formula: C₂₄H₂₇NO₆
• Molecular Weight: 425.481
• Mol file: 258531-75-8.mol

Synonyms:3-trimethylmethylcarbonyl-6-{(E)-[2-(4-methoxycarbonyl)phenyl]ethenyl}pyridoxal monomethyl acetal

Chemical Property of 3-trimethylmethylcarbonyl-6-{(E)-[2-(4-methoxycarbonyl)phenyl]ethenyl}pyridoxal monomethyl acetal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-trimethylmethylcarbonyl-6-{(E)-[2-(4-methoxycarbonyl)phenyl]ethenyl}pyridoxal monomethyl acetal

There total 6 articles about 3-trimethylmethylcarbonyl-6-{(E)-[2-(4-methoxycarbonyl)phenyl]ethenyl}pyridoxal monomethyl acetal 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: 42.0%

methyl 4-iodobenzoate (619-44-3) + 3-trimethylmethylcarbonyl-6-(vinyl)pyridoxal monomethylacetal (258531-70-3) → 3-trimethylmethylcarbonyl-6-{(E)-[2-(4-methoxycarbonyl)phenyl]ethenyl}pyridoxal monomethyl acetal (258531-75-8)

Guidance literature:

With triethylamine; palladium diacetate; tris-(o-tolyl)phosphine; at 100 ℃; for 48h;

DOI:10.1055/s-2000-6228

Reference yield:

7-hydroxy-1-methoxy-6-methyl-1H,3H-furo<3,4-c>pyridine (56583-59-6) → 3-trimethylmethylcarbonyl-6-{(E)-[2-(4-methoxycarbonyl)phenyl]ethenyl}pyridoxal monomethyl acetal (258531-75-8)

Guidance literature:

Multi-step reaction with 5 steps

1: Et₃N / CH₂Cl₂ / 1 h / 25 °C

2: 54 percent / m-CPBA / CH₂Cl₂ / 2 h / 25 °C

3: tetrahydrofuran / 0.5 h / -78 °C

4: 56 percent / tetrahydrofuran / 2 h / -78 - 25 °C

5: 42 percent / Et₃N / Pd(OAc)2, tri-O-tolylphosphine / 48 h / 100 °C

With triethylamine; 3-chloro-benzenecarboperoxoic acid; palladium diacetate; tris-(o-tolyl)phosphine; In tetrahydrofuran; dichloromethane; 1: Esterification / 2: Oxidation / 3: Addition / 4: Grignard reaction / 5: Substitution;

DOI:10.1055/s-2000-6228

Reference yield:

pyridoxal hydrochloride (65-22-5) → 3-trimethylmethylcarbonyl-6-{(E)-[2-(4-methoxycarbonyl)phenyl]ethenyl}pyridoxal monomethyl acetal (258531-75-8)

Guidance literature:

Multi-step reaction with 6 steps

1: NaHCO₃ / 1 h / Heating

2: Et₃N / CH₂Cl₂ / 1 h / 25 °C

3: 54 percent / m-CPBA / CH₂Cl₂ / 2 h / 25 °C

4: tetrahydrofuran / 0.5 h / -78 °C

5: 56 percent / tetrahydrofuran / 2 h / -78 - 25 °C

6: 42 percent / Et₃N / Pd(OAc)2, tri-O-tolylphosphine / 48 h / 100 °C

With sodium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; palladium diacetate; tris-(o-tolyl)phosphine; In tetrahydrofuran; dichloromethane; 1: Cyclization / 2: Esterification / 3: Oxidation / 4: Addition / 5: Grignard reaction / 6: Substitution;

DOI:10.1055/s-2000-6228

upstream raw materials:

methyl 4-iodobenzoate

3-trimethylmethylcarbonyl-6-(vinyl)pyridoxal monomethylacetal

7-hydroxy-1-methoxy-6-methyl-1H,3H-furo<3,4-c>pyridine

pyridoxal hydrochloride