4-Methyl-cyclohex-3-enecarboxylic acid 2-methoxy-3-methyl-cyclopent-2-enyl ester

Base Information

• Chemical Name: 4-Methyl-cyclohex-3-enecarboxylic acid 2-methoxy-3-methyl-cyclopent-2-enyl ester
• CAS No.: 100231-42-3
• Molecular Formula: C₁₅H₂₂O₃
• Molecular Weight: 250.338
• Mol file: 100231-42-3.mol

Synonyms:

Chemical Property of 4-Methyl-cyclohex-3-enecarboxylic acid 2-methoxy-3-methyl-cyclopent-2-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Methyl-cyclohex-3-enecarboxylic acid 2-methoxy-3-methyl-cyclopent-2-enyl ester

There total 2 articles about 4-Methyl-cyclohex-3-enecarboxylic acid 2-methoxy-3-methyl-cyclopent-2-enyl ester 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: 96.0%

4-methylcyclohex-3-enecarboxylic acid (4342-60-3) + 3-methyl-2-methoxycyclopent-2-en-1-ol (100231-40-1) → 4-Methyl-cyclohex-3-enecarboxylic acid 2-methoxy-3-methyl-cyclopent-2-enyl ester (100231-41-2,100231-42-3)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; for 5h; Ambient temperature;

DOI:10.1021/jo00354a018

Reference yield:

2-hydroxy-3-methylcyclopent-2-en-1-one (80-71-7) → 4-Methyl-cyclohex-3-enecarboxylic acid 2-methoxy-3-methyl-cyclopent-2-enyl ester (100231-41-2,100231-42-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 8.11 g / DIBAL / diethyl ether; hexane / 4 h / 0 °C

2: 96 percent / DMAP, DCC / CH₂Cl₂ / 5 h / Ambient temperature

With dmap; diisobutylaluminium hydride; dicyclohexyl-carbodiimide; In diethyl ether; hexane; dichloromethane;

DOI:10.1021/jo00354a018

Reference yield:

4-Methyl-cyclohex-3-enecarboxylic acid 2-methoxy-3-methyl-cyclopent-2-enyl ester (100231-41-2,100231-42-3) → (R)-1-((S)-2-Methoxy-1-methyl-cyclopent-2-enyl)-4-methyl-cyclohex-3-enol

Guidance literature:

Multi-step reaction with 5 steps

2: 100 percent / tetrabutylammonium fluoride / tetrahydrofuran / 6 h

3: 1.2 g / 1 h

4: 1.) LiAlH₄, 2.) Et₃N / 1.) ether, 12 h, 2.) CH₂Cl₂, -10 deg C, 20 min

5: zinc-copper couple, NaI, HMPA / 1,2-dimethoxy-ethane / 48 h / 83 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium aluminium tetrahydride; zinc copper; tetrabutyl ammonium fluoride; triethylamine; sodium iodide; In tetrahydrofuran; 1,2-dimethoxyethane;

DOI:10.1021/jo00354a018

upstream raw materials:

4-methylcyclohex-3-enecarboxylic acid

3-methyl-2-methoxycyclopent-2-en-1-ol

2-hydroxy-3-methylcyclopent-2-en-1-one

Downstream raw materials:

C₂₁H₃₆O₃Si

1-(2-Methoxy-1-methyl-cyclopent-2-enyl)-4-methyl-cyclohex-3-enecarboxylic acid

1-(2-Methoxy-1-methyl-cyclopent-2-enyl)-4-methyl-cyclohex-3-enecarboxylic acid methyl ester

Methanesulfonic acid 1-(2-methoxy-1-methyl-cyclopent-2-enyl)-4-methyl-cyclohex-3-enylmethyl ester

Refernces