Cyclopropanepropanoic acid, a-[(4-fluorophenyl)methylene]-b-oxo-, ethyl ester

Base Information

• Chemical Name: Cyclopropanepropanoic acid, a-[(4-fluorophenyl)methylene]-b-oxo-, ethyl ester
• CAS No.: 137586-94-8
• Molecular Formula: C15H15FO3
• Molecular Weight: 262.281
• Mol file: 137586-94-8.mol

Synonyms:

Chemical Property of Cyclopropanepropanoic acid, a-[(4-fluorophenyl)methylene]-b-oxo-, ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Cyclopropanepropanoic acid, a-[(4-fluorophenyl)methylene]-b-oxo-, ethyl ester

There total 1 articles about Cyclopropanepropanoic acid, a-[(4-fluorophenyl)methylene]-b-oxo-, ethyl ester 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: 82.0%

4-fluorobenzaldehyde (459-57-4) + Ethyl 3-cyclopropyl-3-oxopropionate (24922-02-9) → (Z)-2-Cyclopropanecarbonyl-3-(4-fluoro-phenyl)-acrylic acid ethyl ester (137586-94-8)

Guidance literature:

With piperidine; acetic acid; In benzene; for 22h; Heating;

DOI:10.1021/jm00113a019

Reference yield:

(Z)-2-Cyclopropanecarbonyl-3-(4-fluoro-phenyl)-acrylic acid ethyl ester (137586-94-8) → (S)-4-({2-[2-Cyclopropyl-4-(4-fluoro-phenyl)-5-methyl-6-phenyl-pyridin-3-yl]-ethyl}-methoxy-phosphinoyl)-3-hydroxy-butyric acid methyl ester

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) LiN(TMS)2 / 1.) THF, -78 deg C, 1 h, 2.) THF, 1.5 h

2: NH₄OAc, Cu(OAc)2 / acetic acid / 24 h / Heating

3: LiAlH₄ / tetrahydrofuran / 6 h / Ambient temperature

4: 79 percent / 4-methylmorpholine N-oxide, 4A molecular sieves, tetrapropylammonium perruthenate (TPAP) / CH₂Cl₂ / 0.5 h / Ambient temperature

5: triphenylphosphine / CH₂Cl₂ / 0.42 h / Ambient temperature

6: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

7: 1.) AIBN, tri-n-butyltin hydride, 2.) I₂ / 1.) 120 deg C - 140 deg C, 3 h, 2.) Et₂O, RT, 45 min

8: 1.) tert-butyllithium / 1.) THF, pentane, -100 deg C, 25 min, 2.) THF, pentane, from -100 deg C to -78 deg C, 30 min

9: tetra-n-butylammonium fluoride, HOAc / tetrahydrofuran / 19 h / Ambient temperature

10: H₂ / 10percent Pd/C / methanol / 72 h / 2585.7 Torr

With lithium aluminium tetrahydride; n-butyllithium; tetrapropylammonium perruthennate; copper diacetate; 2,2'-azobis(isobutyronitrile); 4 A molecular sieve; ammonium acetate; tetrabutyl ammonium fluoride; hydrogen; iodine; tert.-butyl lithium; tri-n-butyl-tin hydride; acetic acid; 4-methylmorpholine N-oxide; triphenylphosphine; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; acetic acid;

DOI:10.1021/jm00113a019

Reference yield:

(Z)-2-Cyclopropanecarbonyl-3-(4-fluoro-phenyl)-acrylic acid ethyl ester (137586-94-8) → (S)-4-[[[2-Cyclopropyl-4-(4-fluorophenyl)-5-methyl-6-phenyl-3-pyridinyl]ethyl]hydroxyphosphinyl]-3-hydroxybutanoic acid, disodium salt (135426-94-7)

Guidance literature:

Multi-step reaction with 11 steps

1: 1.) LiN(TMS)2 / 1.) THF, -78 deg C, 1 h, 2.) THF, 1.5 h

2: NH₄OAc, Cu(OAc)2 / acetic acid / 24 h / Heating

3: LiAlH₄ / tetrahydrofuran / 6 h / Ambient temperature

4: 79 percent / 4-methylmorpholine N-oxide, 4A molecular sieves, tetrapropylammonium perruthenate (TPAP) / CH₂Cl₂ / 0.5 h / Ambient temperature

5: triphenylphosphine / CH₂Cl₂ / 0.42 h / Ambient temperature

6: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

7: 1.) AIBN, tri-n-butyltin hydride, 2.) I₂ / 1.) 120 deg C - 140 deg C, 3 h, 2.) Et₂O, RT, 45 min

8: 1.) tert-butyllithium / 1.) THF, pentane, -100 deg C, 25 min, 2.) THF, pentane, from -100 deg C to -78 deg C, 30 min

9: tetra-n-butylammonium fluoride, HOAc / tetrahydrofuran / 19 h / Ambient temperature

10: H₂ / 10percent Pd/C / methanol / 72 h / 2585.7 Torr

11: aq. NaOH / dioxane / Heating

With sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; tetrapropylammonium perruthennate; copper diacetate; 2,2'-azobis(isobutyronitrile); 4 A molecular sieve; ammonium acetate; tetrabutyl ammonium fluoride; hydrogen; iodine; tert.-butyl lithium; tri-n-butyl-tin hydride; acetic acid; 4-methylmorpholine N-oxide; triphenylphosphine; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; acetic acid;

DOI:10.1021/jm00113a019

upstream raw materials:

4-fluorobenzaldehyde

Ethyl 3-cyclopropyl-3-oxopropionate

Downstream raw materials:

2-Cyclopropyl-4-(4-fluorophenyl)-5-methyl-6-phenyl-3-pyridinecarboxaldehyde

2-Cyclopropyl-3-(2-iodoethenyl)-4-(4-fluorophenyl)-5-methyl-6-phenylpyridine

2-Cyclopropyl-3-ethynyl-4-(4-fluoro-phenyl)-5-methyl-6-phenyl-pyridine

2-Cyclopropyl-4-(4-fluorophenyl)-5-methyl-6-phenyl-3-pyridinemethanol

Refernces