(2RS,3RS)-3-(2-ETHOXYPHENOXY)-3-PHENYLPROPENE-1,2-EPOXIDE

Base Information

• Chemical Name: (2RS,3RS)-3-(2-ETHOXYPHENOXY)-3-PHENYLPROPENE-1,2-EPOXIDE
• CAS No.: 98769-72-3
• Molecular Formula: C₁₇H₁₈O₃
• Molecular Weight: 270.328
• Mol file: 98769-72-3.mol

Synonyms:(2RS,3RS)-3-(2-ETHOXYPHENOXY)-3-PHENYLPROPENE-1,2-EPOXIDE;(2R)-rel-2-[(R)-(2-Ethoxyphenoxy)phenylMethyl]oxirane;(R*,R*)-(+/-)-[(2-Ethoxyphenoxy)phenylMethyl]oxirane

Chemical Property of (2RS,3RS)-3-(2-ETHOXYPHENOXY)-3-PHENYLPROPENE-1,2-EPOXIDE

Chemical Property:

• PSA: 30.99000
• LogP: 3.60420
• Solubility.: Chloroform, Dichloromethane, Ethyl Acetate

Purity/Quality:

97% ^*data from raw suppliers

(2RS,3RS)-3-(2-Ethoxyphenoxy)-3-phenylpropene-1,2-epoxide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2RS,3RS)-3-(2-ETHOXYPHENOXY)-3-PHENYLPROPENE-1,2-EPOXIDE

There total 27 articles about (2RS,3RS)-3-(2-ETHOXYPHENOXY)-3-PHENYLPROPENE-1,2-EPOXIDE 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: 65.0%

(+)-(2R,3S)-3-(2-ethoxyphenoxy)-1,2-dihydro-3-phenylpropane (98819-70-6,98769-69-8,127781-32-2) → (-)-(2S,3S)-3-(2-ethoxyphenoxy)-3-phenylpropene-1,2-epoxide (98769-72-3,98819-72-8)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20 ℃; for 24h; Inert atmosphere;

DOI:10.1039/c3ob40853a

Reference yield:

(2E)-3-phenyl-2-propen-1-ol (4407-36-7) → (2RS,3RS)-3-(2-ethoxyphenoxy)-3-phenylpropene-1,2-epoxide (98769-72-3,98819-72-8)

Guidance literature:

Multi-step reaction with 5 steps

1: MCPBA / CH₂Cl₂ / 0 deg C, 1.5 h, then RT, 24 h

2: 1.) NaOH / 1.) H₂O, 70 deg C; 2.) H₂O, 70 deg C, 2.5 h

3: 61 percent / pyridine / 2 h / -10 °C

4: 84 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 - 5 °C

5: 2N NaOH / dioxane / 4 h / Ambient temperature

With sodium hydroxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; In 1,4-dioxane; pyridine; dichloromethane;

DOI:10.1016/S0040-4020(01)96541-X

Reference yield:

(2E)-3-phenyl-2-propen-1-ol (4407-36-7) → (-)-(2S,3S)-3-(2-ethoxyphenoxy)-3-phenylpropene-1,2-epoxide (98769-72-3,98819-72-8)

Guidance literature:

Multi-step reaction with 4 steps

2: Novozymes CaL B / toluene / 17 h / 30 °C

3: triethylamine / toluene / 3 h

4: methyl tributylammonium chloride; sodium hydroxide / water / 3.5 h

With triethylamine; methyl tributylammonium chloride; sodium hydroxide; In water; toluene; 1: Sharpless epoxidation;

DOI:10.1039/c1gc15921f

upstream raw materials:

(2RS,3SR)-3-(2-ethoxyphenoxy)-2-mesyloxy-1-(4-nitrobenzoyloxy)-3-phenylpropane

2-Ethoxyphenol

trans-2,3-epoxy-3-phenylpropan-1-ol

(2RS,3SR)-3-(2-ethoxyphenoxy)-1,2-dihydroxy-3-phenylpropane

Downstream raw materials:

(2RS,3RS)-1-amino-3-(2-ethoxyphenoxy)-2-hydroxy-3-phenylpropane methanesulfonate

(2RS,3RS)-6-<α-(2-ethoxyphenoxy)benzyl>morpholin-3-one

reboxetine

(S,S)-reboxetine

Refernces

• 1、 Assaf, Georges,Checksfield, Graham,Critcher, Doug,Dunn, Peter J.,Field, Stuart,Harris, Laurence J.,Howard, Roger M.,Scotney, Gemma,Scott, Adam,Mathew, Suju,Walker, Geoffrey M. H.,Wilder, Alexander. "The use of environmental metrics to evaluate green chemistry improvements to the synthesis of (S,S)-reboxetine succinate". . p. 123 - 129. Retrieved 2012/04/11.
• 2、 Henegar, Kevin E.,Ball, Cynthia T.,Horvath, Carolyn M.,Maisto, Keith D.,Mancini, Sarah E.. "Process development and scale-up for (±)-reboxetine mesylate". . p. 346 - 353. Retrieved 2012/12/31.