(S)-5-benzyl-3-(4-fluorophenyl)-4,5-dihydroisoxazole

Base Information

• Chemical Name: (S)-5-benzyl-3-(4-fluorophenyl)-4,5-dihydroisoxazole
• CAS No.: 1420031-28-2
• Molecular Formula: C₁₆H₁₄FNO
• Molecular Weight: 255.292
• Mol file: 1420031-28-2.mol

Synonyms:(S)-5-benzyl-3-(4-fluorophenyl)-4,5-dihydroisoxazole

Chemical Property of (S)-5-benzyl-3-(4-fluorophenyl)-4,5-dihydroisoxazole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-5-benzyl-3-(4-fluorophenyl)-4,5-dihydroisoxazole

There total 4 articles about (S)-5-benzyl-3-(4-fluorophenyl)-4,5-dihydroisoxazole 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%

bromobenzene (108-86-1,52753-63-6) + (E)-1-(4-fluorophenyl)but-3-en-1-one oxime → (S)-5-benzyl-3-(4-fluorophenyl)-4,5-dihydroisoxazole (1420031-28-2)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; (R)-N-((S)-(2-(di((3R,5R,7R)-adamantan-1-yl)phosphaneyl)-4,5-dimethoxyphenyl)(phenyl)methyl)-N,2-dimethylpropane-2-sulfinamide; sodium t-butanolate; In toluene; at 70 ℃; for 12h; enantioselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1002/anie.201912408

Reference yield:

4-fluorobenzaldehyde (459-57-4) → (S)-5-benzyl-3-(4-fluorophenyl)-4,5-dihydroisoxazole (1420031-28-2)

Guidance literature:

Multi-step reaction with 4 steps

1: indium / tetrahydrofuran; diethyl ether / 0 °C / Inert atmosphere

2: Jones reagent / diethyl ether / 1 h / 0 - 20 °C / Inert atmosphere

3: sodium acetate; hydroxylamine hydrochloride / water; ethanol / 20 °C / Inert atmosphere

4: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium t-butanolate; (R)-N-((S)-(2-(di((3R,5R,7R)-adamantan-1-yl)phosphaneyl)-4,5-dimethoxyphenyl)(phenyl)methyl)-N,2-dimethylpropane-2-sulfinamide / toluene / 12 h / 70 °C / Inert atmosphere; Schlenk technique

With indium; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; Jones reagent; hydroxylamine hydrochloride; (R)-N-((S)-(2-(di((3R,5R,7R)-adamantan-1-yl)phosphaneyl)-4,5-dimethoxyphenyl)(phenyl)methyl)-N,2-dimethylpropane-2-sulfinamide; sodium acetate; sodium t-butanolate; In tetrahydrofuran; diethyl ether; ethanol; water; toluene;

DOI:10.1002/anie.201912408

Reference yield:

1-(4-fluorophenyl)-3-buten-1-ol (86718-78-7,136185-86-9) → (S)-5-benzyl-3-(4-fluorophenyl)-4,5-dihydroisoxazole (1420031-28-2)

Guidance literature:

Multi-step reaction with 3 steps

1: Jones reagent / diethyl ether / 1 h / 0 - 20 °C / Inert atmosphere

2: sodium acetate; hydroxylamine hydrochloride / water; ethanol / 20 °C / Inert atmosphere

3: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium t-butanolate; (R)-N-((S)-(2-(di((3R,5R,7R)-adamantan-1-yl)phosphaneyl)-4,5-dimethoxyphenyl)(phenyl)methyl)-N,2-dimethylpropane-2-sulfinamide / toluene / 12 h / 70 °C / Inert atmosphere; Schlenk technique

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; Jones reagent; hydroxylamine hydrochloride; (R)-N-((S)-(2-(di((3R,5R,7R)-adamantan-1-yl)phosphaneyl)-4,5-dimethoxyphenyl)(phenyl)methyl)-N,2-dimethylpropane-2-sulfinamide; sodium acetate; sodium t-butanolate; In diethyl ether; ethanol; water; toluene;

DOI:10.1002/anie.201912408

upstream raw materials:

bromobenzene

4-fluorobenzaldehyde

1-(4-fluorophenyl)-3-buten-1-ol

1-(4-fluorophenyl)but-3-en-1-one

Refernces