ethyl α-(ethoxymethylene)-3,4,6-trifluoro-2-methyl-β-oxobenzenepropanoate

Base Information

• Chemical Name: ethyl α-(ethoxymethylene)-3,4,6-trifluoro-2-methyl-β-oxobenzenepropanoate
• CAS No.: 119915-44-5
• Molecular Formula: C₁₅H₁₅F₃O₄
• Molecular Weight: 316.277
• Mol file: 119915-44-5.mol

Synonyms:ethyl α-(ethoxymethylene)-3,4,6-trifluoro-2-methyl-β-oxobenzenepropanoate

Chemical Property of ethyl α-(ethoxymethylene)-3,4,6-trifluoro-2-methyl-β-oxobenzenepropanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl α-(ethoxymethylene)-3,4,6-trifluoro-2-methyl-β-oxobenzenepropanoate

There total 14 articles about ethyl α-(ethoxymethylene)-3,4,6-trifluoro-2-methyl-β-oxobenzenepropanoate 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: 98.0%

ethyl (2,4,5-trifluoro-6-methylbenzoyl)acetate (119915-43-4) + orthoformic acid triethyl ester (122-51-0) → ethyl α-(ethoxymethylene)-3,4,6-trifluoro-2-methyl-β-oxobenzenepropanoate (119915-44-5)

Guidance literature:

With acetic anhydride; for 3h; Heating;

DOI:10.1002/jhet.5570270616

Reference yield:

1-bromo-2,4,5-trifluorobenzene (327-52-6) → ethyl α-(ethoxymethylene)-3,4,6-trifluoro-2-methyl-β-oxobenzenepropanoate (119915-44-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 1) lithium diisopropylamide / 1) THF, -78 deg C, 1 h, 2) up to room temp.

2: 1) lithium diisopropylamide / 1) THF, -78 deg C, 1 h, 2) up to 0 deg C

3: 1) 2.3 M n-BuLi / 1) ether, -78 deg C, 5 min, 2) ether, up to room temp.

4: 89 percent / CsF / acetonitrile / Ambient temperature

5: COCl₂, DMF / CH₂Cl₂ / 2 h / Ambient temperature

6: 1) n-BuLi, bipyridyl / 1) THF, -35 -> -5 deg C, 2) THF, -78 deg C, 1 h

7: 98 percent / acetic anhydride / 3 h / Heating

With [2,2]bipyridinyl; n-butyllithium; acetic anhydride; N,N-dimethyl-formamide; cesium fluoride; lithium diisopropyl amide; In dichloromethane; acetonitrile;

DOI:10.1002/jhet.5570270616

Reference yield:

1-bromo-2,4,5-trifluoro-6-methyl-3-(trimethylsilyl)benzene (132630-85-4) → ethyl α-(ethoxymethylene)-3,4,6-trifluoro-2-methyl-β-oxobenzenepropanoate (119915-44-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 1) 2.3 M n-BuLi / 1) ether, -78 deg C, 5 min, 2) ether, up to room temp.

2: 89 percent / CsF / acetonitrile / Ambient temperature

3: COCl₂, DMF / CH₂Cl₂ / 2 h / Ambient temperature

4: 1) n-BuLi, bipyridyl / 1) THF, -35 -> -5 deg C, 2) THF, -78 deg C, 1 h

5: 98 percent / acetic anhydride / 3 h / Heating

With [2,2]bipyridinyl; n-butyllithium; acetic anhydride; N,N-dimethyl-formamide; cesium fluoride; In dichloromethane; acetonitrile;

DOI:10.1002/jhet.5570270616

upstream raw materials:

ethyl (2,4,5-trifluoro-6-methylbenzoyl)acetate

orthoformic acid triethyl ester

1-bromo-2,4,5-trifluorobenzene

2,4,5-trifluorobenzoic acid

Downstream raw materials:

1-Cyclopropyl-6,7-difluoro-1,4-dihydro-5-methyl-4-oxo-3-quinolinecarboxylic acid

6,7-difluoro-1-(2,4-difluorophenyl)-1,4-dihydro-5-methyl-4-oxo-3-quinolinecarboxylic acid

Refernces

• 1、 Hagen,Domagala. "Synthesis of 5-methyl-4-oxo-quinolinecarboxylic acids". . p. 1609 - 1616. Retrieved 2007/10/02.