(S)-(2Z,4E)-2-benzylidene-6-(3″-methoxyphenoxy)-4-methyl-1-(2′-oxo-4′-phenyloxazolidin-3′-yl)-hex-4-ene-1,3-dione

Base Information

• Chemical Name: (S)-(2Z,4E)-2-benzylidene-6-(3″-methoxyphenoxy)-4-methyl-1-(2′-oxo-4′-phenyloxazolidin-3′-yl)-hex-4-ene-1,3-dione
• CAS No.: 1589071-11-3
• Molecular Formula: C₃₀H₂₇NO₆
• Molecular Weight: 497.547
• Mol file: 1589071-11-3.mol

Synonyms:(S)-(2Z,4E)-2-benzylidene-6-(3″-methoxyphenoxy)-4-methyl-1-(2′-oxo-4′-phenyloxazolidin-3′-yl)-hex-4-ene-1,3-dione

Chemical Property of (S)-(2Z,4E)-2-benzylidene-6-(3″-methoxyphenoxy)-4-methyl-1-(2′-oxo-4′-phenyloxazolidin-3′-yl)-hex-4-ene-1,3-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-(2Z,4E)-2-benzylidene-6-(3″-methoxyphenoxy)-4-methyl-1-(2′-oxo-4′-phenyloxazolidin-3′-yl)-hex-4-ene-1,3-dione

There total 5 articles about (S)-(2Z,4E)-2-benzylidene-6-(3″-methoxyphenoxy)-4-methyl-1-(2′-oxo-4′-phenyloxazolidin-3′-yl)-hex-4-ene-1,3-dione 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: 58.0%

(E)-4-(3'-methoxyphenoxy)-2-methyl-2-butenoyl chloride (1370641-47-6) + (4S)-3-(3-phenyl-2-propyonyl)-4-phenyloxazolidin-2-one (192203-75-1) → (S)-(2Z,4E)-2-benzylidene-6-(3″-methoxyphenoxy)-4-methyl-1-(2′-oxo-4′-phenyloxazolidin-3′-yl)-hex-4-ene-1,3-dione (1589071-11-3)

Guidance literature:

(4S)-3-(3-phenyl-2-propyonyl)-4-phenyloxazolidin-2-one; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; tri-n-butyl-tin hydride; In tetrahydrofuran; at 0 - 20 ℃; for 0.5h; Inert atmosphere;

(E)-4-(3'-methoxyphenoxy)-2-methyl-2-butenoyl chloride; With copper(l) chloride; In tetrahydrofuran; at 20 ℃; for 18h; Inert atmosphere;

DOI:10.1021/jo500040b

Reference yield:

O-methylresorcine (150-19-6) → (S)-(2Z,4E)-2-benzylidene-6-(3″-methoxyphenoxy)-4-methyl-1-(2′-oxo-4′-phenyloxazolidin-3′-yl)-hex-4-ene-1,3-dione (1589071-11-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: potassium carbonate / acetone / Inert atmosphere

2.1: lithium hydroxide; water / tetrahydrofuran / Inert atmosphere

3.1: oxalyl dichloride; N,N-dimethyl-formamide / Inert atmosphere

4.1: tri-n-butyl-tin hydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 0.5 h / 0 - 20 °C / Inert atmosphere

4.2: 18 h / 20 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; oxalyl dichloride; water; tri-n-butyl-tin hydride; potassium carbonate; N,N-dimethyl-formamide; lithium hydroxide; In tetrahydrofuran; acetone;

DOI:10.1021/jo500040b

Reference yield:

C13H16O4 (1562809-94-2) → (S)-(2Z,4E)-2-benzylidene-6-(3″-methoxyphenoxy)-4-methyl-1-(2′-oxo-4′-phenyloxazolidin-3′-yl)-hex-4-ene-1,3-dione (1589071-11-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: lithium hydroxide; water / tetrahydrofuran / Inert atmosphere

2.1: oxalyl dichloride; N,N-dimethyl-formamide / Inert atmosphere

3.1: tri-n-butyl-tin hydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 0.5 h / 0 - 20 °C / Inert atmosphere

3.2: 18 h / 20 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; oxalyl dichloride; water; tri-n-butyl-tin hydride; N,N-dimethyl-formamide; lithium hydroxide; In tetrahydrofuran;

DOI:10.1021/jo500040b

upstream raw materials:

(E)-4-(3'-methoxyphenoxy)-2-methyl-2-butenoyl chloride

(4S)-3-(3-phenyl-2-propyonyl)-4-phenyloxazolidin-2-one

4-bromo-2-methyl-but-2-enoic acid methyl ester

C₁₃H₁₆O₄

Downstream raw materials:

(2R,3S,3aS,9bR)-7-methoxy-9b-methyl-1-oxo-3-phenyl-1,2,3,3a,4,9b-hexahydrocyclopenta[c]chromene-2-carboxylic acid methyl ester