ethyl [1-benzyloxy-2-(4-methylfuran-3-yl)methylcyclopent-2-en-3-yl]propionate

Base Information

• Chemical Name: ethyl [1-benzyloxy-2-(4-methylfuran-3-yl)methylcyclopent-2-en-3-yl]propionate
• CAS No.: 540745-56-0
• Molecular Formula: C₂₃H₂₈O₄
• Molecular Weight: 368.473
• Mol file: 540745-56-0.mol

Synonyms:ethyl [1-benzyloxy-2-(4-methylfuran-3-yl)methylcyclopent-2-en-3-yl]propionate

Chemical Property of ethyl [1-benzyloxy-2-(4-methylfuran-3-yl)methylcyclopent-2-en-3-yl]propionate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl [1-benzyloxy-2-(4-methylfuran-3-yl)methylcyclopent-2-en-3-yl]propionate

There total 4 articles about ethyl [1-benzyloxy-2-(4-methylfuran-3-yl)methylcyclopent-2-en-3-yl]propionate 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: 92.0%

benzyl bromide (100-39-0) + ethyl [1-hydroxy-2-(4-methylfuran-3-yl)methylcyclopent-2-en-3-yl]propionate (540745-54-8) → ethyl [1-benzyloxy-2-(4-methylfuran-3-yl)methylcyclopent-2-en-3-yl]propionate (540745-56-0)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

DOI:10.1016/S0040-4020(03)00181-9

Reference yield:

ethyl 2-(2-bromomethylcyclopent-2-enon-3-yl)propionate (540745-50-4) → ethyl [1-benzyloxy-2-(4-methylfuran-3-yl)methylcyclopent-2-en-3-yl]propionate (540745-56-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 55 percent / 2M K₃PO₄ / Pd(PPh₃)4 / tetrahydrofuran / 2 h / Heating

2: 88 percent / CeCl₃; NaBH₄ / methanol / 0.5 h

3: 92 percent / NaH / dimethylformamide / 2 h / 20 °C

With sodium tetrahydroborate; potassium phosphate; cerium(III) chloride; sodium hydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; 1: Suzuki coupling;

DOI:10.1016/S0040-4020(03)00181-9

Reference yield:

ethyl 2-(2-hydroxymethylcyclopent-2-enon-3-yl)propionate (540745-48-0) → ethyl [1-benzyloxy-2-(4-methylfuran-3-yl)methylcyclopent-2-en-3-yl]propionate (540745-56-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / PBr₃ / diethyl ether / 0.5 h / 0 °C

2: 55 percent / 2M K₃PO₄ / Pd(PPh₃)4 / tetrahydrofuran / 2 h / Heating

3: 88 percent / CeCl₃; NaBH₄ / methanol / 0.5 h

4: 92 percent / NaH / dimethylformamide / 2 h / 20 °C

With sodium tetrahydroborate; potassium phosphate; cerium(III) chloride; phosphorus tribromide; sodium hydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; diethyl ether; N,N-dimethyl-formamide; 2: Suzuki coupling;

DOI:10.1016/S0040-4020(03)00181-9

upstream raw materials:

benzyl bromide

ethyl [1-hydroxy-2-(4-methylfuran-3-yl)methylcyclopent-2-en-3-yl]propionate

ethyl 2-(2-bromomethylcyclopent-2-enon-3-yl)propionate

ethyl 2-(2-hydroxymethylcyclopent-2-enon-3-yl)propionate

Downstream raw materials:

5-benzyloxy-4,5,6,7,8-pentahydro-3,8-dimethylazuleno[6,5-b]furan-9(4H)-one

5-benzyloxy-4,4a,5,6,7-pentahydro-3,8-dimethylazuleno[6,5-b]furan-9(4H)-one

5-benzyloxy-4,4a,5,6,7,9-hexahydro-3,8-dimethylazuleno[6,5-b]furan

2-[3-benzyloxy-2-(4-methyl-furan-3-ylmethyl)-cyclopent-1-enyl]-propionic acid