methyl (E)-2-(3,4-dihydro-2H-pyran-6-carbonyl)-3-(4-methoxyphenyl)acrylate

Base Information

• Chemical Name: methyl (E)-2-(3,4-dihydro-2H-pyran-6-carbonyl)-3-(4-methoxyphenyl)acrylate
• CAS No.: 1007841-60-2
• Molecular Formula: C₁₇H₁₈O₅
• Molecular Weight: 302.327
• Mol file: 1007841-60-2.mol

Synonyms:methyl (E)-2-(3,4-dihydro-2H-pyran-6-carbonyl)-3-(4-methoxyphenyl)acrylate

Chemical Property of methyl (E)-2-(3,4-dihydro-2H-pyran-6-carbonyl)-3-(4-methoxyphenyl)acrylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (E)-2-(3,4-dihydro-2H-pyran-6-carbonyl)-3-(4-methoxyphenyl)acrylate

There total 3 articles about methyl (E)-2-(3,4-dihydro-2H-pyran-6-carbonyl)-3-(4-methoxyphenyl)acrylate 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: 71.0%

4-methoxy-benzaldehyde (123-11-5) + methyl 3-(3,4-dihydro-2H-pyran-6-yl)-3-oxopropanoate → methyl (E)-2-(3,4-dihydro-2H-pyran-6-carbonyl)-3-(4-methoxyphenyl)acrylate (1007841-60-2)

Guidance literature:

methyl 3-(3,4-dihydro-2H-pyran-6-yl)-3-oxopropanoate; With piperidine; acetic acid; In dichloromethane; at 20 ℃; for 0.5h; Inert atmosphere; Molecular sieve; Schlenk technique;

4-methoxy-benzaldehyde; In dichloromethane; at 20 ℃; for 16h; Inert atmosphere; Schlenk technique;

DOI:10.1002/adsc.201701546

Reference yield:

3,4-dihydro-2H-pyran-6-carbonyl chloride → methyl (E)-2-(3,4-dihydro-2H-pyran-6-carbonyl)-3-(4-methoxyphenyl)acrylate (1007841-60-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 0.5 h / 20 °C / Inert atmosphere

2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 - 20 °C / Inert atmosphere

2.2: 1 h / -78 - 20 °C / Inert atmosphere; Molecular sieve

3.1: piperidine; acetic acid / dichloromethane / 0.5 h / 20 °C / Inert atmosphere; Molecular sieve; Schlenk technique

3.2: 16 h / 20 °C / Inert atmosphere; Schlenk technique

With piperidine; acetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;

DOI:10.1002/adsc.201701546

Reference yield:

3,4-dihydro-2H-pyran (110-87-2) → methyl (E)-2-(3,4-dihydro-2H-pyran-6-carbonyl)-3-(4-methoxyphenyl)acrylate (1007841-60-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: tert.-butyl lithium / tetrahydrofuran; pentane / 0.5 h / -78 - 20 °C / Inert atmosphere

1.2: 0.5 h / -78 - 20 °C / Inert atmosphere

2.1: thionyl chloride / dichloromethane / 12 h / 20 °C / Inert atmosphere

3.1: 0.5 h / 20 °C / Inert atmosphere

4.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 - 20 °C / Inert atmosphere

4.2: 1 h / -78 - 20 °C / Inert atmosphere; Molecular sieve

5.1: piperidine; acetic acid / dichloromethane / 0.5 h / 20 °C / Inert atmosphere; Molecular sieve; Schlenk technique

5.2: 16 h / 20 °C / Inert atmosphere; Schlenk technique

With piperidine; thionyl chloride; tert.-butyl lithium; acetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; pentane;

DOI:10.1002/adsc.201701546

upstream raw materials:

4-methoxy-benzaldehyde

3,4-dihydro-2H-pyran

Downstream raw materials:

(5S,6R)-methyl 5-(4-methoxyphenyl)-7-oxo-2,3,4,5,6,7-hexahydrocyclopenta[b]pyran-6-carboxylate