3-(1-Hydroxy-ethyl)-1-(4-methoxy-phenyl)-4-((E)-1-methyl-2-phenyl-vinyl)-azetidin-2-one

Base Information

• Chemical Name: 3-(1-Hydroxy-ethyl)-1-(4-methoxy-phenyl)-4-((E)-1-methyl-2-phenyl-vinyl)-azetidin-2-one
• CAS No.: 100296-98-8
• Molecular Formula: C₂₁H₂₃NO₃
• Molecular Weight: 337.419
• Mol file: 100296-98-8.mol

Synonyms:

Chemical Property of 3-(1-Hydroxy-ethyl)-1-(4-methoxy-phenyl)-4-((E)-1-methyl-2-phenyl-vinyl)-azetidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(1-Hydroxy-ethyl)-1-(4-methoxy-phenyl)-4-((E)-1-methyl-2-phenyl-vinyl)-azetidin-2-one

There total 7 articles about 3-(1-Hydroxy-ethyl)-1-(4-methoxy-phenyl)-4-((E)-1-methyl-2-phenyl-vinyl)-azetidin-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: 35.0%

ethyl 3-hydroxybutyrate (5405-41-4) + (E)-4-methoxy-N-((E)-2-methyl-3-phenylallylidene)aniline (100239-15-4) → 3-(1-Hydroxy-ethyl)-1-(4-methoxy-phenyl)-4-((E)-1-methyl-2-phenyl-vinyl)-azetidin-2-one (100239-22-3,100296-98-8,106399-78-4,106399-79-5,106399-80-8,122673-13-6,122673-15-8)

Guidance literature:

With lithium cyclohexylisopropylamide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; the reaction mixture was quenched at room temp.;

DOI:10.1016/S0040-4039(00)98683-0

Reference yield:

1-(4-Methoxy-phenyl)-4-((E)-1-methyl-2-phenyl-vinyl)-azetidine-2,3-dione (130194-62-6) → 3-(1-Hydroxy-ethyl)-1-(4-methoxy-phenyl)-4-((E)-1-methyl-2-phenyl-vinyl)-azetidin-2-one (100239-22-3,100296-98-8,106399-78-4,106399-79-5,106399-80-8,122673-13-6,122673-15-8)

Guidance literature:

Multi-step reaction with 5 steps

1: KOBu-t / tetrahydrofuran

2: MeSO₂Cl, NEt₃ / CH₂Cl₂

3: 1.) tributyltin hidride, 2.) 5N H₂F₂ / 1.) methylene chloride, 20 h, 2.) methanol

4: Nef reaction

With hydrogen fluoride dimer; potassium tert-butylate; tri-n-butyl-tin hydride; methanesulfonyl chloride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/0040-4039(88)85105-0

Reference yield:

(3S,4R)-3-Hydroxy-1-(4-methoxy-phenyl)-4-((E)-1-methyl-2-phenyl-vinyl)-azetidin-2-one (121766-42-5,131614-11-4) → 3-(1-Hydroxy-ethyl)-1-(4-methoxy-phenyl)-4-((E)-1-methyl-2-phenyl-vinyl)-azetidin-2-one (100239-22-3,100296-98-8,106399-78-4,106399-79-5,106399-80-8,122673-13-6,122673-15-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 90 percent / Me₂SBr₂, NEt₃ / CH₂Cl₂ / 0.75 h / 0 °C

2: KOBu-t / tetrahydrofuran

3: MeSO₂Cl, NEt₃ / CH₂Cl₂

4: 1.) tributyltin hidride, 2.) 5N H₂F₂ / 1.) methylene chloride, 20 h, 2.) methanol

5: Nef reaction

With hydrogen fluoride dimer; potassium tert-butylate; tri-n-butyl-tin hydride; dimethylbromosulphonium bromide; methanesulfonyl chloride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/0040-4039(88)85105-0

upstream raw materials:

ethyl 3-hydroxybutyrate

(E)-4-methoxy-N-((E)-2-methyl-3-phenylallylidene)aniline

3-Acetyl-1-(4-methoxy-phenyl)-4-((E)-1-methyl-2-phenyl-vinyl)-azetidin-2-one

1-(4-Methoxy-phenyl)-4-((E)-1-methyl-2-phenyl-vinyl)-azetidine-2,3-dione

Refernces

• 1、 Georg,Gill,Gerhardt. "3-(1'-hydroxyethyl)-2-azetidinones from 3-hydroxybutyrates and N-arylaldimines". . p. 3903 - 3906. Retrieved 2007/10/02.