(5R)-5-[(1R,2Z,4E)-1-(4-methoxybenzyloxy)hexa-2,4-dienyl]-4,5-dihydro-2(3H)-furanone

Base Information

• Chemical Name: (5R)-5-[(1R,2Z,4E)-1-(4-methoxybenzyloxy)hexa-2,4-dienyl]-4,5-dihydro-2(3H)-furanone
• CAS No.: 901144-14-7
• Molecular Formula: C₁₈H₂₂O₄
• Molecular Weight: 302.37
• Mol file: 901144-14-7.mol

Synonyms:(5R)-5-[(1R,2Z,4E)-1-(4-methoxybenzyloxy)hexa-2,4-dienyl]-4,5-dihydro-2(3H)-furanone

Chemical Property of (5R)-5-[(1R,2Z,4E)-1-(4-methoxybenzyloxy)hexa-2,4-dienyl]-4,5-dihydro-2(3H)-furanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5R)-5-[(1R,2Z,4E)-1-(4-methoxybenzyloxy)hexa-2,4-dienyl]-4,5-dihydro-2(3H)-furanone

There total 8 articles about (5R)-5-[(1R,2Z,4E)-1-(4-methoxybenzyloxy)hexa-2,4-dienyl]-4,5-dihydro-2(3H)-furanone 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: 87.0%

(5R)-5-[(1R,2Z)-1-(4-methoxybenzyloxy)-3-iodoprop-2-enyl]-4,5-dihydro-2(3H)-furanone (901144-08-9) + (E)-propenylboronic acid (6336-44-3,7547-96-8,88982-39-2,7547-97-9) → (5R)-5-[(1R,2Z,4E)-1-(4-methoxybenzyloxy)hexa-2,4-dienyl]-4,5-dihydro-2(3H)-furanone (901144-14-7)

Guidance literature:

With cesium fluoride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In toluene;

DOI:10.1016/j.tetlet.2006.04.075

Reference yield:

(5R)-5-[(1S)-2,3-dibromo-1-(4-methoxybenzyloxy)propyl]-4,5-dihydro-2(3H)-furanone (901142-84-5) → (5R)-5-[(1R,2Z,4E)-1-(4-methoxybenzyloxy)hexa-2,4-dienyl]-4,5-dihydro-2(3H)-furanone (901144-14-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 72 percent / DBU / dimethylformamide / 85 h / 80 °C

2: 80 percent / NIS; AgNO₃ / acetone / 1 h / 0 °C

3: 100 percent / o-nitrophenylsulfonylhydrazide; triethylamine / tetrahydrofuran; propan-2-ol / 19 h / 20 °C

4: 87 percent / CsF / PdCl₂(dppf) / toluene / 15 h / 20 °C

With N-iodo-succinimide; 2-nitrobenzenesulfonyl hydrazide; silver nitrate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; cesium fluoride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; N,N-dimethyl-formamide; isopropyl alcohol; acetone; toluene; 4: Suzuki-Miyaura coupling;

DOI:10.1246/bcsj.80.578

Reference yield:

(5R)-5-[(1R)-1-(4-methoxybenzyloxy)prop-2-enyl]-4,5-dihydro-2(3H)-furanone (901143-94-0) → (5R)-5-[(1R,2Z,4E)-1-(4-methoxybenzyloxy)hexa-2,4-dienyl]-4,5-dihydro-2(3H)-furanone (901144-14-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 100 percent / pyridine*HBr₃; pyridine / CH₂Cl₂ / 12 h / 0 °C

2: 72 percent / DBU / dimethylformamide / 85 h / 80 °C

3: 80 percent / NIS; AgNO₃ / acetone / 1 h / 0 °C

4: 100 percent / o-nitrophenylsulfonylhydrazide; triethylamine / tetrahydrofuran; propan-2-ol / 19 h / 20 °C

5: 87 percent / CsF / PdCl₂(dppf) / toluene / 15 h / 20 °C

With pyridine; N-iodo-succinimide; pyridinium perbromide hydrobromide; 2-nitrobenzenesulfonyl hydrazide; silver nitrate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; cesium fluoride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; acetone; toluene; 5: Suzuki-Miyaura coupling;

DOI:10.1246/bcsj.80.578

upstream raw materials:

(5R)-5-[(1R,2Z)-1-(4-methoxybenzyloxy)-3-iodoprop-2-enyl]-4,5-dihydro-2(3H)-furanone

(E)-propenylboronic acid

(5R)-5-[(1R)-1-(4-methoxybenzyloxy)prop-2-enyl]-4,5-dihydro-2(3H)-furanone

(5R)-5-[(1R)-1-(4-methoxybenzyloxy)prop-2-ynyl]-4,5-dihydro-2(3H)-furanone