8-methoxy-4-(2-nitro-vinyl)-2,3,5,6-tetrahydro-benzo[1,2-b;5,4-b']difuran

Base Information

• Chemical Name: 8-methoxy-4-(2-nitro-vinyl)-2,3,5,6-tetrahydro-benzo[1,2-b;5,4-b']difuran
• CAS No.: 194787-75-2
• Molecular Formula: C₁₃H₁₃NO₅
• Molecular Weight: 263.25
• Mol file: 194787-75-2.mol

Synonyms:

Chemical Property of 8-methoxy-4-(2-nitro-vinyl)-2,3,5,6-tetrahydro-benzo[1,2-b;5,4-b']difuran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 8-methoxy-4-(2-nitro-vinyl)-2,3,5,6-tetrahydro-benzo[1,2-b;5,4-b']difuran

There total 5 articles about 8-methoxy-4-(2-nitro-vinyl)-2,3,5,6-tetrahydro-benzo[1,2-b;5,4-b']difuran 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: 91.0%

nitromethane (75-52-5) + 8-methoxy-2,3,5,6-tetrahydro-benzo[1,2-b;5,4-b']difuran-4-carbaldehyde (194787-73-0) → 8-methoxy-4-(2-nitro-vinyl)-2,3,5,6-tetrahydro-benzo[1,2-b;5,4-b']difuran (194787-75-2)

Guidance literature:

With sodium acetate; In acetic acid; at 110 ℃; for 6h;

DOI:10.1021/ol034228d

Reference yield:

methyl 3,5-dihydroxy-4-methoxybenzoate (24093-81-0) → 8-methoxy-4-(2-nitro-vinyl)-2,3,5,6-tetrahydro-benzo[1,2-b;5,4-b']difuran (194787-75-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 20 percent / Na₂CO₃; [IrCl(cod)]2 / toluene / 100 °C

2.1: 92 percent / sodium bis(2-methoxyethoxy)aluminum hydride; pyrrolidine; t-BuOK / toluene; tetrahydrofuran / 0.17 h / 0 °C

3.1: 95 percent / 4 Angstroem molecular sieves / toluene / 12 h / 23 °C

4.1: dicyclohexyl ferrocenyl phosphine; [RhCl(coe)2]2 / toluene / 2 h / 150 °C

4.2: 65 percent / aq. HCl / ethyl acetate / 3 h

5.1: 91 percent / NaOAc / acetic acid / 6 h / 110 °C

With pyrrolidine; bis(1,5-cyclooctadiene)diiridium(I) dichloride; dicyclohexyl ferrocenyl phosphine; [RhCl(coe)2]2; 4 A molecular sieve; potassium tert-butylate; sodium acetate; sodium carbonate; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; acetic acid; toluene; 5.1: Henry reaction;

DOI:10.1021/ol034228d

Reference yield:

4-methoxy-3,5-bis-vinyloxy-benzaldehyde (524941-80-8) → 8-methoxy-4-(2-nitro-vinyl)-2,3,5,6-tetrahydro-benzo[1,2-b;5,4-b']difuran (194787-75-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 95 percent / 4 Angstroem molecular sieves / toluene / 12 h / 23 °C

2.1: dicyclohexyl ferrocenyl phosphine; [RhCl(coe)2]2 / toluene / 2 h / 150 °C

2.2: 65 percent / aq. HCl / ethyl acetate / 3 h

3.1: 91 percent / NaOAc / acetic acid / 6 h / 110 °C

With dicyclohexyl ferrocenyl phosphine; [RhCl(coe)2]2; 4 A molecular sieve; sodium acetate; In acetic acid; toluene; 3.1: Henry reaction;

DOI:10.1021/ol034228d

upstream raw materials:

nitromethane

8-methoxy-2,3,5,6-tetrahydro-benzo[1,2-b;5,4-b']difuran-4-carbaldehyde

methyl 3,5-dihydroxy-4-methoxybenzoate

4-methoxy-3,5-bis-vinyloxy-benzaldehyde