2-[(R)-3-(2,6-dimethoxycyclohexa-2,5-dienyl)-1-methylpropyl]-5-methoxybenzofuran

Base Information

• Chemical Name: 2-[(R)-3-(2,6-dimethoxycyclohexa-2,5-dienyl)-1-methylpropyl]-5-methoxybenzofuran
• CAS No.: 449727-91-7
• Molecular Formula: C₂₁H₂₆O₄
• Molecular Weight: 342.435
• Mol file: 449727-91-7.mol

Synonyms:2-[(R)-3-(2,6-dimethoxycyclohexa-2,5-dienyl)-1-methylpropyl]-5-methoxybenzofuran

Chemical Property of 2-[(R)-3-(2,6-dimethoxycyclohexa-2,5-dienyl)-1-methylpropyl]-5-methoxybenzofuran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[(R)-3-(2,6-dimethoxycyclohexa-2,5-dienyl)-1-methylpropyl]-5-methoxybenzofuran

There total 10 articles about 2-[(R)-3-(2,6-dimethoxycyclohexa-2,5-dienyl)-1-methylpropyl]-5-methoxybenzofuran 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: 85.0%

C8H11LiO2 (113379-12-7) + 2-((R)-3-iodo-1-methylpropyl)-5-methoxybenzofuran (449727-89-3) → 2-[(R)-3-(2,6-dimethoxycyclohexa-2,5-dienyl)-1-methylpropyl]-5-methoxybenzofuran (449727-91-7)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1002/1521-3773(20020503)41:9<1569::AID-ANIE1569>3.0.CO;2-8

Reference yield: 67.0%

1,5-dimethoxy-1,4-cyclohexadiene (37567-78-5) + 2-((R)-3-iodo-1-methylpropyl)-5-methoxybenzofuran (449727-89-3) → 2-[(R)-3-(2,6-dimethoxycyclohexa-2,5-dienyl)-1-methylpropyl]-5-methoxybenzofuran (449727-91-7) + 3-methoxy-2-[(R)-3-(5-methoxybenzofuran-2-yl)butyl]cyclohex-3-enone

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; In tetrahydrofuran; pentane; at -78 - 20 ℃; for 1.75h;

DOI:10.1016/j.tet.2004.07.041

Reference yield:

acetic acid 2-bromo-4-methoxyphenyl ester (449727-85-9) → 2-[(R)-3-(2,6-dimethoxycyclohexa-2,5-dienyl)-1-methylpropyl]-5-methoxybenzofuran (449727-91-7)

Guidance literature:

Multi-step reaction with 6 steps

1: Pd(PPh₃)2Cl₂; CuI; Et₃N / acetonitrile / 16 h / Heating

2: TFA / 0.17 h

3: K₂CO₃ / methanol / 5 h / Heating

4: Et₃N / tetrahydrofuran / 1 h / 0 °C

5: NaI / acetone / 2 h / Heating

6: 67 percent / n-BuLi; HMPA / pentane; tetrahydrofuran / 1.75 h / -78 - 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; n-butyllithium; potassium carbonate; triethylamine; trifluoroacetic acid; sodium iodide; In tetrahydrofuran; methanol; acetone; acetonitrile; pentane; 1: Sonogashira coupling;

DOI:10.1016/j.tet.2004.07.041

upstream raw materials:

C₈H₁₁LiO₂

2-((R)-3-iodo-1-methylpropyl)-5-methoxybenzofuran

1,5-dimethoxy-1,4-cyclohexadiene

2-bromo-4-methoxyphenol

Downstream raw materials:

trifluoromethanesulfonic acid 2-[(R)-3-(5-methoxybenzofuran-2-yl)butyl]-3-oxocyclohex-1-enyl ester

2-[(R)-3-(5-Methoxy-benzofuran-2-yl)-butyl]-cyclohexane-1,3-dione