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

Base Information

• Chemical Name: 5-benzyloxy-4,4a,5,6,7-pentahydro-3,8-dimethylazuleno[6,5-b]furan-9(4H)-one
• CAS No.: 540745-60-6
• Molecular Formula: C₂₁H₂₂O₃
• Molecular Weight: 322.404
• Mol file: 540745-60-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

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

5-benzyloxy-4,5,6,7,8-pentahydro-3,8-dimethylazuleno[6,5-b]furan-9(4H)-one (540745-58-2) → 5-benzyloxy-4,4a,5,6,7-pentahydro-3,8-dimethylazuleno[6,5-b]furan-9(4H)-one (540745-60-6)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at -78 ℃; for 30h;

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

Reference yield:

ethyl 2-(2-hydroxymethylcyclopent-2-enon-3-yl)propionate (540745-48-0) → 5-benzyloxy-4,4a,5,6,7-pentahydro-3,8-dimethylazuleno[6,5-b]furan-9(4H)-one (540745-60-6)

Guidance literature:

Multi-step reaction with 7 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

5: aq. NaOH / methanol / 10 h / Heating

6: 113 mg / TFAA / bis-(2-hydroxy-ethyl) ether / 6 h / 0 °C

7: 65 percent / DBU / CH₂Cl₂ / 30 h / -78 °C

With sodium hydroxide; sodium tetrahydroborate; potassium phosphate; cerium(III) chloride; phosphorus tribromide; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic anhydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; diethylene glycol; 2: Suzuki coupling / 6: Friedel-Crafts cyclization;

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

Reference yield:

ethyl 2-(2-bromomethylcyclopent-2-enon-3-yl)propionate (540745-50-4) → 5-benzyloxy-4,4a,5,6,7-pentahydro-3,8-dimethylazuleno[6,5-b]furan-9(4H)-one (540745-60-6)

Guidance literature:

Multi-step reaction with 6 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

4: aq. NaOH / methanol / 10 h / Heating

5: 113 mg / TFAA / bis-(2-hydroxy-ethyl) ether / 6 h / 0 °C

6: 65 percent / DBU / CH₂Cl₂ / 30 h / -78 °C

With sodium hydroxide; sodium tetrahydroborate; potassium phosphate; cerium(III) chloride; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic anhydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; diethylene glycol; 1: Suzuki coupling / 5: Friedel-Crafts cyclization;

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

upstream raw materials:

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

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

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

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

Downstream raw materials:

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