2-Oxazolidinone, 3-[(2E)-1-oxo-3-[4-(trifluoromethyl)phenyl]-2-propenyl]-4-phenyl-, (4S)-

Base Information

• Chemical Name: 2-Oxazolidinone, 3-[(2E)-1-oxo-3-[4-(trifluoromethyl)phenyl]-2-propenyl]-4-phenyl-, (4S)-
• CAS No.: 264626-04-2
• Molecular Formula: C19H14F3NO3
• Molecular Weight: 361.32
• Mol file: 264626-04-2.mol

Synonyms:

Chemical Property of 2-Oxazolidinone, 3-[(2E)-1-oxo-3-[4-(trifluoromethyl)phenyl]-2-propenyl]-4-phenyl-, (4S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Oxazolidinone, 3-[(2E)-1-oxo-3-[4-(trifluoromethyl)phenyl]-2-propenyl]-4-phenyl-, (4S)-

There total 2 articles about 2-Oxazolidinone, 3-[(2E)-1-oxo-3-[4-(trifluoromethyl)phenyl]-2-propenyl]-4-phenyl-, (4S)- 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:

3-<4'-(trifluoromethyl)phenyl>-2-propenoic acid (2062-26-2,87212-84-8,16642-92-5) → (S)-4-phenyl-3-{(E)-3-[4-(trifluoromethyl)phenyl]prop-2-enoyl}-1,3-oxazolidin-2-one (264626-04-2)

Guidance literature:

Multi-step reaction with 2 steps

1: SOCl₂ / 5 h / Heating

2: 98 percent / Et₃N; LiCl / CH₂Cl₂ / 1 h / 20 °C

With thionyl chloride; triethylamine; lithium chloride; In dichloromethane;

DOI:10.1002/1522-2675(200211)85:11<3616::AID-HLCA3616>3.0.CO;2-O

Reference yield:

→ (S)-4-phenyl-3-{(E)-3-[4-(trifluoromethyl)phenyl]prop-2-enoyl}-1,3-oxazolidin-2-one (264626-04-2)

Guidance literature:

Reference yield: 97.0%

Ni(OC(O)CH2NC(C6H5)C6H4NC(O)CHCH2CH2CH2NCH2C6H5) + (S)-4-phenyl-3-{(E)-3-[4-(trifluoromethyl)phenyl]prop-2-enoyl}-1,3-oxazolidin-2-one (264626-04-2) → Ni(OC(O)CH(CH(C6H4CF3)CH2C(O)NC(O)OCH2CHC6H5)NC(C6H5)C6H4NC(O)CHCH2CH2CH2NCH2C6H5)

Guidance literature:

With catalyst: DBU; In N,N-dimethyl-formamide; N-(enoyl)-4-phenyl-1,3-oxazolidin-2-one (1.05-1.1 equiv.) added with stirring to suspn. of Ni complex in DMF; stirred at room temp. (22°C) for 10-15 min; DBU (15 mol%) added dropwise; 5 min; monitored by thin-layer chromy.; poured into icy 5% aq. acetic acid; stirred; filtered; ppt. washed with H2O; dried in vac.;

DOI:10.1021/ja0535561

upstream raw materials:

3-<4'-(trifluoromethyl)phenyl>-2-propenoic acid

Downstream raw materials:

(2S,3R)-3-(p-trifluoromethylphenyl)pyroglutamic acid