2-Oxo-6-[2-oxo-6-(toluene-4-sulfonyloxy)-hex-3-ynyl]-cyclohexanecarboxylic acid methyl ester

Base Information

• Chemical Name: 2-Oxo-6-[2-oxo-6-(toluene-4-sulfonyloxy)-hex-3-ynyl]-cyclohexanecarboxylic acid methyl ester
• CAS No.: 130975-20-1
• Molecular Formula: C₂₁H₂₄O₇S
• Molecular Weight: 420.483
• Mol file: 130975-20-1.mol

Synonyms:2-Oxo-6-[2-oxo-6-(toluene-4-sulfonyloxy)-hex-3-ynyl]-cyclohexanecarboxylic acid methyl ester

Chemical Property of 2-Oxo-6-[2-oxo-6-(toluene-4-sulfonyloxy)-hex-3-ynyl]-cyclohexanecarboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Oxo-6-[2-oxo-6-(toluene-4-sulfonyloxy)-hex-3-ynyl]-cyclohexanecarboxylic acid methyl ester

There total 7 articles about 2-Oxo-6-[2-oxo-6-(toluene-4-sulfonyloxy)-hex-3-ynyl]-cyclohexanecarboxylic 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: 90.0%

2,2-Dimethoxy-6-[2-oxo-6-(toluene-4-sulfonyloxy)-hex-3-ynyl]-cyclohexanecarboxylic acid methyl ester (130975-19-8,130975-24-5) → 2-Oxo-6-[2-oxo-6-(toluene-4-sulfonyloxy)-hex-3-ynyl]-cyclohexanecarboxylic acid methyl ester (130975-20-1)

Guidance literature:

With toluene-4-sulfonic acid; In acetone; at 23 ℃; for 36h;

DOI:10.1139/v90-296

Reference yield:

3-butyn-1-yl p-toluenesulfonate (23418-85-1) → 2-Oxo-6-[2-oxo-6-(toluene-4-sulfonyloxy)-hex-3-ynyl]-cyclohexanecarboxylic acid methyl ester (130975-20-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) n-BuLi / 1) THF, hexane, -78 deg C, 45 min, 2) THF, -78 deg C, 1.5h

2: 93 percent / acetone / 0.08 h / 0 °C / Jones reagent

3: 90 percent / p-TsOH / acetone / 36 h / 23 °C

With n-butyllithium; toluene-4-sulfonic acid; In acetone;

DOI:10.1139/v90-296

Reference yield:

2-Allyl-6-oxo-cyclohexanecarboxylic acid methyl ester (130975-16-5) → 2-Oxo-6-[2-oxo-6-(toluene-4-sulfonyloxy)-hex-3-ynyl]-cyclohexanecarboxylic acid methyl ester (130975-20-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 84 percent / p-TsOH / methanol / 12 h / 23 °C

2: 1) O₃, 2) PPh₃ / 1) CH₂Cl₂, -78 deg C, 2) r.t., 2h

3: 1) n-BuLi / 1) THF, hexane, -78 deg C, 45 min, 2) THF, -78 deg C, 1.5h

4: 93 percent / acetone / 0.08 h / 0 °C / Jones reagent

5: 90 percent / p-TsOH / acetone / 36 h / 23 °C

With n-butyllithium; toluene-4-sulfonic acid; ozone; triphenylphosphine; In methanol; acetone;

DOI:10.1139/v90-296

upstream raw materials:

2,2-Dimethoxy-6-[2-oxo-6-(toluene-4-sulfonyloxy)-hex-3-ynyl]-cyclohexanecarboxylic acid methyl ester

2-carbomethoxy-2-cyclohexenone

2-Allyl-6-oxo-cyclohexanecarboxylic acid methyl ester

3-butyn-1-yl p-toluenesulfonate

Downstream raw materials:

2-Oxo-6-(2-oxo-hex-5-en-3-ynyl)-cyclohexanecarboxylic acid methyl ester

(4aR,8aS)-4,7-Dioxo-5-vinyl-1,3,4,7,8,8a-hexahydro-2H-naphthalene-4a-carboxylic acid methyl ester