(R,E)-3-[3-(2,5-dimethoxy-4-methylphenyl)acryloyl]-4-phenyloxazolidin-2-one

Base Information

• Chemical Name: (R,E)-3-[3-(2,5-dimethoxy-4-methylphenyl)acryloyl]-4-phenyloxazolidin-2-one
• CAS No.: 1329428-58-1
• Molecular Formula: C₂₁H₂₁NO₅
• Molecular Weight: 367.401
• Mol file: 1329428-58-1.mol

Synonyms:(R,E)-3-[3-(2,5-dimethoxy-4-methylphenyl)acryloyl]-4-phenyloxazolidin-2-one

Chemical Property of (R,E)-3-[3-(2,5-dimethoxy-4-methylphenyl)acryloyl]-4-phenyloxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R,E)-3-[3-(2,5-dimethoxy-4-methylphenyl)acryloyl]-4-phenyloxazolidin-2-one

There total 1 articles about (R,E)-3-[3-(2,5-dimethoxy-4-methylphenyl)acryloyl]-4-phenyloxazolidin-2-one 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: 81.0%

1-bromo-2,5-dimethoxy-4-methylbenzene (13321-74-9) + (4R)-3-acryloyl-4-phenyl-1,3-oxazolidin-2-one (133940-76-8) → (R,E)-3-[3-(2,5-dimethoxy-4-methylphenyl)acryloyl]-4-phenyloxazolidin-2-one (1329428-58-1)

Guidance literature:

With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine; In water; acetonitrile; at 80 ℃; for 2h; Inert atmosphere;

DOI:10.1016/j.tet.2011.03.064

Reference yield: 71.0%

(R,E)-3-[3-(2,5-dimethoxy-4-methylphenyl)acryloyl]-4-phenyloxazolidin-2-one (1329428-58-1) + methylmagnesium bromide (75-16-1) → (R)-3-[(R)-3-(2,5-dimethoxy-4-methylphenyl)butanoyl]-4-phenyloxazolidin-2-one (1260083-80-4) + (R)-3-[(S)-3-(2,5-dimethoxy-4-methylphenyl)butanoyl]-4-phenyloxazolidin-2-one

Guidance literature:

methylmagnesium bromide; With copper(I) bromide dimethylsulfide complex; dimethylsulfide; In tetrahydrofuran; at -4 ℃; for 0.166667h; Inert atmosphere;

(R,E)-3-[3-(2,5-dimethoxy-4-methylphenyl)acryloyl]-4-phenyloxazolidin-2-one; In tetrahydrofuran; at -20 ℃; for 0.5h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;

DOI:10.1016/j.tet.2011.03.064

Reference yield:

(R,E)-3-[3-(2,5-dimethoxy-4-methylphenyl)acryloyl]-4-phenyloxazolidin-2-one (1329428-58-1) → (R)-1,4-dimethoxy-2-(5-methoxypent-4-en-2-yl)-5-methylbenzene (1329428-62-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: copper(I) bromide dimethylsulfide complex; dimethylsulfide / tetrahydrofuran / 0.17 h / -4 °C / Inert atmosphere

1.2: 0.5 h / -20 °C / Inert atmosphere

2.1: sodium tetrahydroborate / tetrahydrofuran; water / 3.5 h / 50 °C / Inert atmosphere

3.1: pyridinium chlorochromate / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

4.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere

4.2: 1 h / 0 - 20 °C / Inert atmosphere

With sodium tetrahydroborate; copper(I) bromide dimethylsulfide complex; dimethylsulfide; sodium hexamethyldisilazane; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; water; 4.2: Wittig reaction;

DOI:10.1016/j.tet.2011.03.064

upstream raw materials:

1-bromo-2,5-dimethoxy-4-methylbenzene

(4R)-3-acryloyl-4-phenyl-1,3-oxazolidin-2-one

Downstream raw materials:

(R)-3-(2,5-dimethoxy-4-methylphenyl)butanoic acid

(R)-1,4-dimethoxy-2-(5-methoxypent-4-en-2-yl)-5-methylbenzene

(R)-4-(2,5-dimethoxy-4-methylphenyl)pentanal

(3S,6R)-6-(2,5-dimethoxy-4-methylphenyl)-2-methylheptane-2,3-diol