benzyl 2,5,5-trimethyl-5,6-dihydro-4H-cyclopentafuran-4-carboxylate

Base Information

• Chemical Name: benzyl 2,5,5-trimethyl-5,6-dihydro-4H-cyclopentafuran-4-carboxylate
• CAS No.: 122948-16-7
• Molecular Formula: C₁₈H₂₀O₃
• Molecular Weight: 284.355
• Mol file: 122948-16-7.mol

Synonyms:benzyl 2,5,5-trimethyl-5,6-dihydro-4H-cyclopentafuran-4-carboxylate

Chemical Property of benzyl 2,5,5-trimethyl-5,6-dihydro-4H-cyclopentafuran-4-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 2,5,5-trimethyl-5,6-dihydro-4H-cyclopentafuran-4-carboxylate

There total 1 articles about benzyl 2,5,5-trimethyl-5,6-dihydro-4H-cyclopentafuran-4-carboxylate 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: 98.0%

5-diazo-6,7-dihydro-2,6,6-trimethyl-4(5H)-benzofuranone (107365-20-8) + benzyl alcohol (100-51-6,185532-71-2) → benzyl 2,5,5-trimethyl-5,6-dihydro-4H-cyclopentafuran-4-carboxylate (122948-16-7)

Guidance literature:

With 2,4,6-trimethyl-pyridine; at 180 - 190 ℃; for 0.25h;

DOI:10.1021/jo00285a013

Reference yield:

benzyl 2,5,5-trimethyl-5,6-dihydro-4H-cyclopentafuran-4-carboxylate (122948-16-7) → 4-<(benzyloxy)methyl>-5,6-dihydro-2,5,5-trimethyl-4H-cyclopentafuran (122948-00-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / LiAlH₄ / tetrahydrofuran / Ambient temperature

2: 1.) sodium hydride, tetra n-butylammonium iodide / 1.) THF, 30 min, 2.) room temp., 14 h

With lithium aluminium tetrahydride; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran;

DOI:10.1021/jo00285a013

Reference yield:

benzyl 2,5,5-trimethyl-5,6-dihydro-4H-cyclopentafuran-4-carboxylate (122948-16-7) → 2-(2-oxopropyl)-3-<(benzyloxy)methyl>-4,4-dimethylcyclopentanone (122948-04-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / LiAlH₄ / tetrahydrofuran / Ambient temperature

2: 1.) sodium hydride, tetra n-butylammonium iodide / 1.) THF, 30 min, 2.) room temp., 14 h

3: 82 percent / 80percent aq. acetic acid, conc. H₂SO₄ / 1 h / 70 - 80 °C

With lithium aluminium tetrahydride; sulfuric acid; tetra-(n-butyl)ammonium iodide; sodium hydride; acetic acid; In tetrahydrofuran;

DOI:10.1021/jo00285a013

upstream raw materials:

5-diazo-6,7-dihydro-2,6,6-trimethyl-4(5H)-benzofuranone

benzyl alcohol

Downstream raw materials:

4-<(benzyloxy)methyl>-5,6-dihydro-2,5,5-trimethyl-4H-cyclopentafuran

2-(2-oxopropyl)-3-<(benzyloxy)methyl>-4,4-dimethylcyclopentanone