allyl 1-(4-ethoxy-4-oxobutyl)-2-oxo-4-(phenylthio)cyclohex-3-enecarboxylate

Base Information

• Chemical Name: allyl 1-(4-ethoxy-4-oxobutyl)-2-oxo-4-(phenylthio)cyclohex-3-enecarboxylate
• CAS No.: 900493-84-7
• Molecular Formula: C₂₂H₂₆O₅S
• Molecular Weight: 402.511
• Mol file: 900493-84-7.mol

Synonyms:allyl 1-(4-ethoxy-4-oxobutyl)-2-oxo-4-(phenylthio)cyclohex-3-enecarboxylate

Chemical Property of allyl 1-(4-ethoxy-4-oxobutyl)-2-oxo-4-(phenylthio)cyclohex-3-enecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl 1-(4-ethoxy-4-oxobutyl)-2-oxo-4-(phenylthio)cyclohex-3-enecarboxylate

There total 4 articles about allyl 1-(4-ethoxy-4-oxobutyl)-2-oxo-4-(phenylthio)cyclohex-3-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: 61.0%

allyl 2-oxo-4-(phenylthio)cyclohex-3-enecarboxylate (900493-69-8) + Ethyl 4-bromobutyrate (2969-81-5) → allyl 1-(4-ethoxy-4-oxobutyl)-2-oxo-4-(phenylthio)cyclohex-3-enecarboxylate (900493-84-7)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; caesium carbonate; In N,N-dimethyl-formamide;

DOI:10.1002/anie.200504421

Reference yield:

3-(phenylsulfanyl)cyclohex-2-en-1-one (75717-39-4) → allyl 1-(4-ethoxy-4-oxobutyl)-2-oxo-4-(phenylthio)cyclohex-3-enecarboxylate (900493-84-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-Buli; diisopropylamine / toluene / 0.5 h / -78 °C

1.2: 75 percent / toluene / -78 - 23 °C

2.1: 61 percent / Cs₂CO₃; tetrabutylammonium iodide / dimethylformamide

With n-butyllithium; tetra-(n-butyl)ammonium iodide; caesium carbonate; diisopropylamine; In N,N-dimethyl-formamide; toluene;

DOI:10.1002/anie.200504421

Reference yield:

1,3-cylohexanedione (504-02-9) → allyl 1-(4-ethoxy-4-oxobutyl)-2-oxo-4-(phenylthio)cyclohex-3-enecarboxylate (900493-84-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Et₃N; methanesulfonyl chloride / acetonitrile / 1 h / 0 - 25 °C

1.2: 85 percent / Et₃N / acetonitrile / 14 h / 0 - 25 °C

2.1: n-Buli; diisopropylamine / toluene / 0.5 h / -78 °C

2.2: 75 percent / toluene / -78 - 23 °C

3.1: 61 percent / Cs₂CO₃; tetrabutylammonium iodide / dimethylformamide

With n-butyllithium; tetra-(n-butyl)ammonium iodide; caesium carbonate; methanesulfonyl chloride; triethylamine; diisopropylamine; In N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1002/anie.200504421

upstream raw materials:

allyl 2-oxo-4-(phenylthio)cyclohex-3-enecarboxylate

Ethyl 4-bromobutyrate

3-(phenylsulfanyl)cyclohex-2-en-1-one

1,3-cylohexanedione