(±)-methyl 6-methyl-2-(((trifluoromethyl)sulfonyl)oxy)cyclohex-1-enecarboxylate

Base Information

• Chemical Name: (±)-methyl 6-methyl-2-(((trifluoromethyl)sulfonyl)oxy)cyclohex-1-enecarboxylate
• CAS No.: 152564-11-9
• Molecular Formula: C₁₀H₁₃F₃O₅S
• Molecular Weight: 302.271
• Mol file: 152564-11-9.mol

Synonyms:(±)-methyl 6-methyl-2-(((trifluoromethyl)sulfonyl)oxy)cyclohex-1-enecarboxylate

Chemical Property of (±)-methyl 6-methyl-2-(((trifluoromethyl)sulfonyl)oxy)cyclohex-1-enecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (±)-methyl 6-methyl-2-(((trifluoromethyl)sulfonyl)oxy)cyclohex-1-enecarboxylate

There total 5 articles about (±)-methyl 6-methyl-2-(((trifluoromethyl)sulfonyl)oxy)cyclohex-1-enecarboxylate 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%

trifluoromethylsulfonic anhydride (358-23-6) + (±)-methyl 2-methyl-6-oxocyclohexanecarboxylate (93493-96-0) → (±)-methyl 6-methyl-2-(((trifluoromethyl)sulfonyl)oxy)cyclohex-1-enecarboxylate (152564-11-9)

Guidance literature:

(±)-methyl 2-methyl-6-oxocyclohexanecarboxylate; With sodium hydride; In dichloromethane; at 0 ℃; for 0.5h; Inert atmosphere;

trifluoromethylsulfonic anhydride; In dichloromethane; at 20 ℃; Inert atmosphere;

DOI:10.1021/jacs.5b02946

Reference yield:

methyl 3-oxo-6-octenoate (110874-83-4) → (±)-methyl 6-methyl-2-(((trifluoromethyl)sulfonyl)oxy)cyclohex-1-enecarboxylate (152564-11-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: copper dichloride; PdCl₂(MeCN)2; chloro-trimethyl-silane / 1,4-dioxane / 14 h / 55 °C

2.1: sodium hydride / mineral oil; dichloromethane / 0 °C

2.2: 0 - 20 °C

With chloro-trimethyl-silane; PdCl₂(MeCN)2; sodium hydride; copper dichloride; In 1,4-dioxane; dichloromethane; mineral oil;

DOI:10.1021/ol503541z

Reference yield:

ethyl acetoacetate (141-97-9) → (±)-methyl 6-methyl-2-(((trifluoromethyl)sulfonyl)oxy)cyclohex-1-enecarboxylate (152564-11-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C

1.2: 0.17 h / 0 °C

1.3: 2 h / 0 - 20 °C

2.1: copper dichloride; PdCl₂(MeCN)2; chloro-trimethyl-silane / 1,4-dioxane / 14 h / 55 °C

3.1: sodium hydride / mineral oil; dichloromethane / 0 °C

3.2: 0 - 20 °C

With chloro-trimethyl-silane; PdCl₂(MeCN)2; sodium hydride; copper dichloride; In tetrahydrofuran; 1,4-dioxane; dichloromethane; mineral oil;

DOI:10.1021/ol503541z

upstream raw materials:

trifluoromethylsulfonic anhydride

(±)-methyl 2-methyl-6-oxocyclohexanecarboxylate

2-carbomethoxy-2-cyclohexenone

methyl 3-oxo-6-octenoate

Downstream raw materials:

methyl 6-methyl-2-(trimethylstannyl)-1-cyclohexenecarboxylate