Eupomatilone 3

Base Information

• Chemical Name: Eupomatilone 3
• CAS No.: 139006-77-2
• Molecular Formula: C₂₃H₂₆O₈
• Molecular Weight: 430.455
• Mol file: 139006-77-2.mol

Synonyms:

Chemical Property of Eupomatilone 3

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Eupomatilone 3

There total 7 articles about Eupomatilone 3 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:

5-[7-methoxy-6-(3,4,5-trimethoxyphenyl)-benzo[1,3]dioxol-5-yl]-4-methyl-5H-furan-2-one (870094-83-0) + methyl iodide (74-88-4) → eupomatilone-3 + eupomatilone-3 (139006-77-2)

Guidance literature:

5-[7-methoxy-6-(3,4,5-trimethoxyphenyl)-benzo[1,3]dioxol-5-yl]-4-methyl-5H-furan-2-one; With polymethylhydrosiloxane; copper dichloride; sodium t-butanolate; (S)-(-)-(6,6’-dimethoxybiphenyl-2,2’-diyl)bis(diphenylphosphine); In tetrahydrofuran; dichloromethane; tert-butyl alcohol; at 20 ℃; for 24h;

With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 4.5h;

methyl iodide; In tetrahydrofuran; at -78 - -20 ℃; Title compound not separated from byproducts;

DOI:10.1002/anie.200501890

Reference yield:

[7-methoxy-6-(3,4,5-trimethoxyphenyl)-benzo[1,3]dioxol-5-yl]methanol (870094-81-8) → eupomatilone-3 (139006-77-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: MnO₂ / CH₂Cl₂ / 2 h / 20 °C

2.1: iPrMgCl / tetrahydrofuran; diethyl ether / -20 °C

2.2: 76 percent / tetrahydrofuran; diethyl ether / 1 h / -40 °C

3.1: polymethylhydrosiloxane; copper(II) chloride dihydrate; sodium tert-butoxide / (S)-2,2'-bis(diphenylphosphino)-6,6'-dimethoxybiphenyl / tetrahydrofuran; CH₂Cl₂; 2-methyl-propan-2-ol / 24 h / 20 °C

3.2: sodium hexamethyldisilazide / tetrahydrofuran / 4.5 h / -78 °C

3.3: tetrahydrofuran / -78 - -20 °C

With manganese(IV) oxide; polymethylhydrosiloxane; isopropylmagnesium chloride; copper dichloride; sodium t-butanolate; (S)-(-)-(6,6’-dimethoxybiphenyl-2,2’-diyl)bis(diphenylphosphine); In tetrahydrofuran; diethyl ether; dichloromethane; tert-butyl alcohol;

DOI:10.1002/anie.200501890

Reference yield:

7-methoxy-6-(3,4,5-trimethoxyphenyl)-benzo[1,3]dioxole-5-carboxaldehyde (870094-82-9) → eupomatilone-3 (139006-77-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: iPrMgCl / tetrahydrofuran; diethyl ether / -20 °C

1.2: 76 percent / tetrahydrofuran; diethyl ether / 1 h / -40 °C

2.1: polymethylhydrosiloxane; copper(II) chloride dihydrate; sodium tert-butoxide / (S)-2,2'-bis(diphenylphosphino)-6,6'-dimethoxybiphenyl / tetrahydrofuran; CH₂Cl₂; 2-methyl-propan-2-ol / 24 h / 20 °C

2.2: sodium hexamethyldisilazide / tetrahydrofuran / 4.5 h / -78 °C

2.3: tetrahydrofuran / -78 - -20 °C

With polymethylhydrosiloxane; isopropylmagnesium chloride; copper dichloride; sodium t-butanolate; (S)-(-)-(6,6’-dimethoxybiphenyl-2,2’-diyl)bis(diphenylphosphine); In tetrahydrofuran; diethyl ether; dichloromethane; tert-butyl alcohol;

DOI:10.1002/anie.200501890

upstream raw materials:

5-[7-methoxy-6-(3,4,5-trimethoxyphenyl)-benzo[1,3]dioxol-5-yl]-4-methyl-5H-furan-2-one

methyl iodide

7-methoxy-6-(3,4,5-trimethoxyphenyl)-benzo[1,3]dioxole-5-carboxaldehyde

[7-methoxy-6-(3,4,5-trimethoxyphenyl)-benzo[1,3]dioxol-5-yl]methanol