methyl 3-({2,13,15,26-tetraoxa-1,14(1,3,2)-dibenzena-27(2,6)-pyridinabicyclo[12.12.1]heptacosaphan-1⁵-yl}methyloxy)benzoate

Base Information

• Chemical Name: methyl 3-({2,13,15,26-tetraoxa-1,14(1,3,2)-dibenzena-27(2,6)-pyridinabicyclo[12.12.1]heptacosaphan-1⁵-yl}methyloxy)benzoate
• CAS No.: 934990-73-5
• Molecular Formula: C₄₆H₅₇NO₇
• Molecular Weight: 735.961
• Mol file: 934990-73-5.mol

Synonyms:methyl 3-({2,13,15,26-tetraoxa-1,14(1,3,2)-dibenzena-27(2,6)-pyridinabicyclo[12.12.1]heptacosaphan-1⁵-yl}methyloxy)benzoate

Chemical Property of methyl 3-({2,13,15,26-tetraoxa-1,14(1,3,2)-dibenzena-27(2,6)-pyridinabicyclo[12.12.1]heptacosaphan-1⁵-yl}methyloxy)benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3-({2,13,15,26-tetraoxa-1,14(1,3,2)-dibenzena-27(2,6)-pyridinabicyclo[12.12.1]heptacosaphan-1⁵-yl}methyloxy)benzoate

There total 13 articles about methyl 3-({2,13,15,26-tetraoxa-1,14(1,3,2)-dibenzena-27(2,6)-pyridinabicyclo[12.12.1]heptacosaphan-1⁵-yl}methyloxy)benzoate 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: 65.0%

15-(hydroxymethyl)-2,13,15,26-tetraoxa-1,14(1,3,2)-dibenzena-27(2,6)-pyridinabicyclo[12.12.1]heptacosaphane (934990-67-7) + methyl 3-hydroxybenzoate (19438-10-9) → methyl 3-({2,13,15,26-tetraoxa-1,14(1,3,2)-dibenzena-27(2,6)-pyridinabicyclo[12.12.1]heptacosaphan-15-yl}methyloxy)benzoate (934990-73-5)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 18h;

DOI:10.1002/ejoc.200600842

Reference yield:

2,6-Dibromopyridine (626-05-1) → methyl 3-({2,13,15,26-tetraoxa-1,14(1,3,2)-dibenzena-27(2,6)-pyridinabicyclo[12.12.1]heptacosaphan-15-yl}methyloxy)benzoate (934990-73-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 73 percent / aq. Na₂CO₃ / Pd(PPh₃)4 / 1,2-dimethoxy-ethane / 16 h / Heating

2: 84 percent / aq. Na₂CO₃; Ba(OH)2*H₂O / Pd(PPh₃)4 / 1,2-dimethoxy-ethane; H₂O / 19 h / Heating

3: 98 percent / p-TsOH / methanol / 1.5 h / Heating

4: 89 percent / benzylidenebis(tricyclohexylphosphane)dichlororuthenium / CH₂Cl₂ / 21 h / 20 °C

5: 96 percent / H₂ / Pd/C / methanol; CHCl₃ / 21 h / 20 °C

6: 65 percent / PPh₃; diisopropyl azodicarboxylate / tetrahydrofuran / 18 h / 20 °C

With barium dihydroxide; di-isopropyl azodicarboxylate; hydrogen; sodium carbonate; toluene-4-sulfonic acid; triphenylphosphine; palladium on activated charcoal; Grubbs catalyst first generation; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; chloroform; water; 1: Suzuki coupling / 2: Suzuki coupling / 6: Mitsunobu coupling;

DOI:10.1002/ejoc.200600842

Reference yield:

2-[2,6-bis(hex-5-enyloxy)phenyl]-6-bromopyridine (934991-02-3) → methyl 3-({2,13,15,26-tetraoxa-1,14(1,3,2)-dibenzena-27(2,6)-pyridinabicyclo[12.12.1]heptacosaphan-15-yl}methyloxy)benzoate (934990-73-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 84 percent / aq. Na₂CO₃; Ba(OH)2*H₂O / Pd(PPh₃)4 / 1,2-dimethoxy-ethane; H₂O / 19 h / Heating

2: 98 percent / p-TsOH / methanol / 1.5 h / Heating

3: 89 percent / benzylidenebis(tricyclohexylphosphane)dichlororuthenium / CH₂Cl₂ / 21 h / 20 °C

4: 96 percent / H₂ / Pd/C / methanol; CHCl₃ / 21 h / 20 °C

5: 65 percent / PPh₃; diisopropyl azodicarboxylate / tetrahydrofuran / 18 h / 20 °C

With barium dihydroxide; di-isopropyl azodicarboxylate; hydrogen; sodium carbonate; toluene-4-sulfonic acid; triphenylphosphine; palladium on activated charcoal; Grubbs catalyst first generation; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; chloroform; water; 1: Suzuki coupling / 5: Mitsunobu coupling;

DOI:10.1002/ejoc.200600842

upstream raw materials:

1⁵-(hydroxymethyl)-2,13,15,26-tetraoxa-1,14(1,3,2)-dibenzena-27(2,6)-pyridinabicyclo[12.12.1]heptacosaphane

methyl 3-hydroxybenzoate

2,6-Dibromopyridine

2-[2,6-bis(hex-5-enyloxy)phenyl]-6-bromopyridine