2,6-Dimethyl-6-{2-[2-oxo-cyclopent-(Z)-ylidene]-ethyl}-cyclohex-1-enecarboxylic acid methyl ester

Base Information

• Chemical Name: 2,6-Dimethyl-6-{2-[2-oxo-cyclopent-(Z)-ylidene]-ethyl}-cyclohex-1-enecarboxylic acid methyl ester
• CAS No.: 98127-22-1
• Molecular Formula: C₁₇H₂₄O₃
• Molecular Weight: 276.376
• Mol file: 98127-22-1.mol

Synonyms:2,6-Dimethyl-6-{2-[2-oxo-cyclopent-(Z)-ylidene]-ethyl}-cyclohex-1-enecarboxylic acid methyl ester

Chemical Property of 2,6-Dimethyl-6-{2-[2-oxo-cyclopent-(Z)-ylidene]-ethyl}-cyclohex-1-enecarboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,6-Dimethyl-6-{2-[2-oxo-cyclopent-(Z)-ylidene]-ethyl}-cyclohex-1-enecarboxylic acid methyl ester

There total 7 articles about 2,6-Dimethyl-6-{2-[2-oxo-cyclopent-(Z)-ylidene]-ethyl}-cyclohex-1-enecarboxylic acid methyl 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: 73.0%

(α-ketocyclopentylidene)triphenylphosphorane (2136-76-7) + 2,6-Dimethyl-6-(2-oxo-ethyl)-cyclohex-1-enecarboxylic acid methyl ester (98127-19-6) → 2,6-Dimethyl-6-{2-[2-oxo-cyclopent-(Z)-ylidene]-ethyl}-cyclohex-1-enecarboxylic acid methyl ester (98127-22-1)

Guidance literature:

In benzene; for 24h; Heating;

DOI:10.1021/jo00221a027

Reference yield:

3,4-dihydro-6-methyl-2H-pyran-2-one (3740-59-8) → 2,6-Dimethyl-6-{2-[2-oxo-cyclopent-(Z)-ylidene]-ethyl}-cyclohex-1-enecarboxylic acid methyl ester (98127-22-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 0.5 h, 2.) THF, a) -78 deg C, 4 h, b) 25 deg C, 8 h

2: 1.) CuI / 1.) THF, -20 deg C, 2.) THF, -78 deg C, 1 h

3: 1.) NaH / 1.) ether, 10 min, 2.) ether, 2 h

4: 1.) CuI / 1.) ether, -20 deg C, 2.) ether, 4 h

5: 1.) O₃, 2.) Me₂S / 1.) MeOH, CH₂Cl₂, -78 deg C, 2.) MeOH, CH₂Cl₂, 25 deg C, overnight

6: 73 percent / benzene / 24 h / Heating

With copper(l) iodide; dimethylsulfide; sodium hydride; ozone; lithium diisopropyl amide; In benzene;

DOI:10.1021/jo00221a027

Reference yield:

5-ketohexanoic acid (3128-06-1) → 2,6-Dimethyl-6-{2-[2-oxo-cyclopent-(Z)-ylidene]-ethyl}-cyclohex-1-enecarboxylic acid methyl ester (98127-22-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 80 percent / SOCl₂ / benzene / 10 h / Heating

2: 1.) lithium diisopropylamide / 1.) THF, -78 deg C, 0.5 h, 2.) THF, a) -78 deg C, 4 h, b) 25 deg C, 8 h

3: 1.) CuI / 1.) THF, -20 deg C, 2.) THF, -78 deg C, 1 h

4: 1.) NaH / 1.) ether, 10 min, 2.) ether, 2 h

5: 1.) CuI / 1.) ether, -20 deg C, 2.) ether, 4 h

6: 1.) O₃, 2.) Me₂S / 1.) MeOH, CH₂Cl₂, -78 deg C, 2.) MeOH, CH₂Cl₂, 25 deg C, overnight

7: 73 percent / benzene / 24 h / Heating

With copper(l) iodide; thionyl chloride; dimethylsulfide; sodium hydride; ozone; lithium diisopropyl amide; In benzene;

DOI:10.1021/jo00221a027

upstream raw materials:

(α-ketocyclopentylidene)triphenylphosphorane

2,6-Dimethyl-6-(2-oxo-ethyl)-cyclohex-1-enecarboxylic acid methyl ester

3,4-dihydro-6-methyl-2H-pyran-2-one

5-ketohexanoic acid

Downstream raw materials:

2,6-Dimethyl-6-[2-(5-oxo-cyclopent-1-enyl)-ethyl]-cyclohex-1-enecarboxylic acid methyl ester