(4S,1'E)-3-(2'-phenylethenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one

Base Information

• Chemical Name: (4S,1'E)-3-(2'-phenylethenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one
• CAS No.: 636580-91-1
• Molecular Formula: C₁₉H₁₉NO₂
• Molecular Weight: 293.365
• Mol file: 636580-91-1.mol

Synonyms:(4S,1'E)-3-(2'-phenylethenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one

Chemical Property of (4S,1'E)-3-(2'-phenylethenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,1'E)-3-(2'-phenylethenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one

There total 6 articles about (4S,1'E)-3-(2'-phenylethenyl)-5,5-dimethyl-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: 85.0%

phenylacetaldehyde (122-78-1) + (4S)-5,5-dimethyl-4-phenyl-1,3-oxazolidin-2-one (168297-84-5) → (4S,1'E)-3-(2'-phenylethenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one (636580-91-1)

Guidance literature:

With toluene-4-sulfonic acid; In toluene; for 3h; Heating;

DOI:10.1055/s-2003-41425

Reference yield: 76.0%

(S)-N(3)-[(triphenylphosphonium)methyl]-4-phenyl-5,5-dimethyloxazolidin-2-one chloride (1067232-41-0) + benzaldehyde (100-52-7) → (S)-N(3)-methyl-4-phenyl-5,5-dimethyloxazolidin-2-one (1067232-46-5) + (S,Z)-N(3)-(2'-phenylethenyl)-4-phenyl-5,5-dimethyloxazolidin-2-one (1067232-44-3) + (4S,1'E)-3-(2'-phenylethenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one (636580-91-1)

Guidance literature:

(S)-N⁽³⁾-[(triphenylphosphonium)methyl]-4-phenyl-5,5-dimethyloxazolidin-2-one chloride; With potassium tert-butylate; In tetrahydrofuran; at -78 ℃; for 0.5h;

benzaldehyde; In tetrahydrofuran; at -78 ℃; for 24h; Further stages.;

DOI:10.1016/j.tet.2008.07.012

Reference yield:

(S,E)-N(3)-(3',3'-dimethyl-but-1'-enyl)-4-phenyl-5,5-dimethyloxazolidin-2-one (636580-96-6) → (4S,1'E)-3-(2'-phenylethenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one (636580-91-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / CHCl₃ / 0 - 20 °C

2: LiAlH₄ / tetrahydrofuran / 20 °C

3: 85 percent / p-TSA / toluene / 3 h / Heating

With lithium aluminium tetrahydride; toluene-4-sulfonic acid; In tetrahydrofuran; chloroform; toluene;

DOI:10.1055/s-2003-41425

upstream raw materials:

phenylacetaldehyde

(4S)-5,5-dimethyl-4-phenyl-1,3-oxazolidin-2-one

(S,E)-N⁽³⁾-(3',3'-dimethyl-but-1'-enyl)-4-phenyl-5,5-dimethyloxazolidin-2-one

(S,E)-N⁽³⁾-(3'-phenyl-prop-1'-enyl)-4-phenyl-5,5-dimethyloxazolidin-2-one

Downstream raw materials:

(4S,1'R,2'S)-N⁽³⁾-[1'-(m-chlorobenzoyl)-2'-hydroxy-2'-phenyl-ethan-1'-yl]-4-phenyl-5,5-dimethyloxazolidin-2-one

(4S,2'R,3'S)-N⁽³⁾-(3'-phenyloxiran-2'-yl)-4-phenyl-5,5-dimethyloxazolidin-2-one

(S)-1-phenyl-1,2-ethanediol

(4S)-5,5-dimethyl-4-phenyl-1,3-oxazolidin-2-one