ethyl (+/-)-(Z)-2-acetamido-5-(1-methyl-3-oxocyclohexyl)-2-pentenoate

Base Information

• Chemical Name: ethyl (+/-)-(Z)-2-acetamido-5-(1-methyl-3-oxocyclohexyl)-2-pentenoate
• CAS No.: 172921-86-7
• Molecular Formula: C₁₆H₂₅NO₄
• Molecular Weight: 295.379
• Mol file: 172921-86-7.mol

Synonyms:ethyl (+/-)-(Z)-2-acetamido-5-(1-methyl-3-oxocyclohexyl)-2-pentenoate

Chemical Property of ethyl (+/-)-(Z)-2-acetamido-5-(1-methyl-3-oxocyclohexyl)-2-pentenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (+/-)-(Z)-2-acetamido-5-(1-methyl-3-oxocyclohexyl)-2-pentenoate

There total 7 articles about ethyl (+/-)-(Z)-2-acetamido-5-(1-methyl-3-oxocyclohexyl)-2-pentenoate 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: 82.0%

ethyl (+/-)-(Z)-2-acetamido-5-(7-methyl-1,4-dioxaspiro<4.5>dec-7-yl)-2-pentenoate (172921-89-0) → ethyl (+/-)-(Z)-2-acetamido-5-(1-methyl-3-oxocyclohexyl)-2-pentenoate (172921-86-7)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; for 11h; Ambient temperature;

DOI:10.1021/jo951532e

Reference yield:

2-acetamido-3-ethoxy-3-oxopropanoic acid (54681-67-3,187868-53-7) → ethyl (+/-)-(Z)-2-acetamido-5-(1-methyl-3-oxocyclohexyl)-2-pentenoate (172921-86-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 64 percent / Ac₂O, pyridine / 5.6 h / Ambient temperature

2: 82 percent / aq. HCl / tetrahydrofuran / 11 h / Ambient temperature

With pyridine; hydrogenchloride; acetic anhydride; In tetrahydrofuran;

DOI:10.1021/jo951532e

Reference yield:

3-Ethoxycyclohex-2-en-1-one (5323-87-5) → ethyl (+/-)-(Z)-2-acetamido-5-(1-methyl-3-oxocyclohexyl)-2-pentenoate (172921-86-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 70 percent / diethyl ether / 1.3 h / Heating

2: 88 percent / diethyl ether / 2.6 h / -30 - -10 °C

3: 95 percent / (MeO)3CH, p-TsOH*H₂O / benzene / 3.25 h / Ambient temperature

4: 1.) O₃, NaHCO₃, 2.) Me₂S / 1.) CH₂Cl₂, MeOH, -78 deg C, 1.5 h, 2.) -78 deg C, 45 min; room temperature, 12.7 h

5: 64 percent / Ac₂O, pyridine / 5.6 h / Ambient temperature

6: 82 percent / aq. HCl / tetrahydrofuran / 11 h / Ambient temperature

With pyridine; hydrogenchloride; dimethylsulfide; acetic anhydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; ozone; trimethyl orthoformate; In tetrahydrofuran; diethyl ether; benzene;

DOI:10.1021/jo951532e

upstream raw materials:

ethyl (+/-)-(Z)-2-acetamido-5-(7-methyl-1,4-dioxaspiro<4.5>dec-7-yl)-2-pentenoate

2-acetamido-3-ethoxy-3-oxopropanoic acid

3-Ethoxycyclohex-2-en-1-one

(+/-)-3-methyl-3-(4-methyl-3-pentenyl)cyclohexanone