[R-(E)]-alpha-[3-[2-(7-Chloro-2-quinolinyl)ethenyl]phenyl]-2-(1-hydroxy-1-methylethyl)benzenepropanol

Base Information

• Chemical Name: [R-(E)]-alpha-[3-[2-(7-Chloro-2-quinolinyl)ethenyl]phenyl]-2-(1-hydroxy-1-methylethyl)benzenepropanol
• CAS No.: 150026-75-8
• Molecular Formula: C29H28ClNO2
• Molecular Weight: 458
• Mol file: 150026-75-8.mol

Synonyms:Benzenepropanol,a-[3-[2-(7-chloro-2-quinolinyl)ethenyl]phenyl]-2-(1-hydroxy-1-methylethyl)-,[R-(E)]- (9CI);

Chemical Property of [R-(E)]-alpha-[3-[2-(7-Chloro-2-quinolinyl)ethenyl]phenyl]-2-(1-hydroxy-1-methylethyl)benzenepropanol

Chemical Property:

• Melting Point: 78-83°C
• Boiling Point: 636.8 °C at 760 mmHg
• Flash Point: 338.9 °C
• PSA: 53.35000
• Density: 1.244 g/cm³
• LogP: 6.95220
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

99.5% ^*data from raw suppliers

2-[3-(R)-[3-(2-(7-Chloro-2-quinolinyl)ethenyl)phenyl]-3-hydroxypropyl]phenyl-2-propanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Intermediate in the preparation of (S)-Montelukast.

Technology Process of [R-(E)]-alpha-[3-[2-(7-Chloro-2-quinolinyl)ethenyl]phenyl]-2-(1-hydroxy-1-methylethyl)benzenepropanol

There total 11 articles about [R-(E)]-alpha-[3-[2-(7-Chloro-2-quinolinyl)ethenyl]phenyl]-2-(1-hydroxy-1-methylethyl)benzenepropanol 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:

methylmagnesium chloride (676-58-4) + -2-<3-<3-<2-(7-chloro-2-quinolinyl)ethenyl>phenyl>-3-hydroxypropyl>benzoic acid methyl ester (150026-72-5) → (2-(2-(3-(3(R)-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-hydroxypropyl)phenyl)-2-propanol) (150026-75-8)

Guidance literature:

methylmagnesium chloride; -2-<3-<3-<2-(7-chloro-2-quinolinyl)ethenyl>phenyl>-3-hydroxypropyl>benzoic acid methyl ester; In toluene; at -5 - 15 ℃; for 18h;

With water; sodium hydrogencarbonate; In toluene; at 20 - 30 ℃; for 3h;

Reference yield:

trans-1-{3-[2-(7-chloroquinolin-2-yl)ethenyl]phenyl}-3-[2-(1-hydroxy-1-methylethyl)phenyl]propan-1-one (1258428-71-5) → (2-(2-(3-(3(R)-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-hydroxypropyl)phenyl)-2-propanol) (150026-75-8) + (S,E)-1-(3-(2-(7-chloroquinolin-2-yl)vinyl)phenyl)-3-(2-(2-hydroxypropan-2-yl)phenyl)propan-1-ol (287930-77-2)

Guidance literature:

With [((S)-PhanePhos)-((R,R)-DACH)RuCl₂]; potassium tert-butylate; hydrogen; In tetrahydrofuran; isopropyl alcohol; at 25 ℃; for 4h; under 4425.44 - 6000.6 Torr; Reagent/catalyst; enantioselective reaction;

DOI:10.1021/acs.joc.5b00197

Reference yield:

2-bromobenzoic-acid (88-65-3) → (2-(2-(3-(3(R)-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-hydroxypropyl)phenyl)-2-propanol) (150026-75-8) + (S,E)-1-(3-(2-(7-chloroquinolin-2-yl)vinyl)phenyl)-3-(2-(2-hydroxypropan-2-yl)phenyl)propan-1-ol (287930-77-2)

Guidance literature:

Multi-step reaction with 6 steps

1: sulfuric acid / 20.25 h / 0 °C / Reflux

2: tetrahydrofuran / 0 - 20 °C / Inert atmosphere

3: dmap / n-heptane / 100 °C / Inert atmosphere

4: N-ethyl-N,N-diisopropylamine; tris-(o-tolyl)phosphine; triethylamine / acetonitrile / 36 h / 75 - 80 °C / Inert atmosphere

5: potassium hydroxide / tetrahydrofuran; methanol / 20 - 45 °C / Inert atmosphere

6: potassium tert-butylate; [((S)-PhanePhos)-((R,R)-DACH)RuCl₂]; hydrogen / tetrahydrofuran; isopropyl alcohol / 4 h / 25 °C / 4425.44 - 6000.6 Torr

With dmap; sulfuric acid; [((S)-PhanePhos)-((R,R)-DACH)RuCl₂]; potassium tert-butylate; hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; tris-(o-tolyl)phosphine; potassium hydroxide; In tetrahydrofuran; methanol; n-heptane; isopropyl alcohol; acetonitrile; 1: |Fischer-Speier Esterification;

DOI:10.1021/acs.joc.5b00197

upstream raw materials:

methylmagnesium chloride

-2-<3-<3-<2-(7-chloro-2-quinolinyl)ethenyl>phenyl>-3-hydroxypropyl>benzoic acid methyl ester

2-bromobenzoic-acid

2-Iodobenzoic acid

Downstream raw materials:

(S)-benzenepropanol α-[3-[2-(7-chloro-2-quinolinyl)ethenyl]phenyl]-2-(1-hydroxy-1-methyl ethyl)-α-methane sulfonate

Refernces

• 1、 -. "PREPARATION OF MONTELUKAST AND ITS SALTS". Page/Page column 33-34. . Retrieved 2008/12/05.
• 2、 -. "Fluorinated hydroxyalkylquinoline acids as leukotriene antagonists". . . Retrieved 2008/06/13.