methyl (E)-3-methyl-4-oxobut-2-enoate

Base Information

• Chemical Name: methyl (E)-3-methyl-4-oxobut-2-enoate
• CAS No.: 153812-94-3
• Molecular Formula: C6H8O3
• Molecular Weight: 128.128
• European Community (EC) Number: 609-870-1,604-928-2
• DSSTox Substance ID: DTXSID301019392
• Nikkaji Number: J1.350.101G,J1.360.215H
• Wikidata: Q76416305
• Mol file: 153812-94-3.mol

Synonyms:40835-18-5;methyl (E)-3-methyl-4-oxobut-2-enoate;(E)-Methyl 3-methyl-4-oxobut-2-enoate;3-Formylisocrotonic acid methyl ester;153812-94-3;METHYL 3-METHYL-4-OXOBUT-2-ENOATE;2-Butenoic acid, 3-methyl-4-oxo-, methyl ester;SCHEMBL4800118;DTXSID301019392;AMY39195;METHYL3-METHYL-4-OXOBUT-2-ENOATE;methyl (2E)-3-methyl-4-oxo-2-butenoate;3-Methyl-4-oxo-2-butenoic acid methyl ester

Chemical Property of methyl (E)-3-methyl-4-oxobut-2-enoate

Chemical Property:

• Vapor Pressure: 0.37mmHg at 25°C
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 128.047344113
• Heavy Atom Count: 9
• Complexity: 146

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CC(=O)OC)C=O
• Isomeric SMILES: C/C(=C\C(=O)OC)/C=O

Technology Process of methyl (E)-3-methyl-4-oxobut-2-enoate

There total 2 articles about methyl (E)-3-methyl-4-oxobut-2-enoate 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:

methyl 2-methyl-3-<(trimethylsilyl)oxy>-1-cyclopropanecarboxylate (82884-40-0) → methyl 3-formyl-cis-crotonate (153812-94-3)

Guidance literature:

With bromine; triethylamine; Yield given. Multistep reaction; 1) -78 deg C, 10 min, dichloromethane, 2) -78 deg C to room temp.;

DOI:10.1016/S0040-4039(00)87247-0

Reference yield:

→ methyl 3-formyl-cis-crotonate (153812-94-3)

Guidance literature:

entspr. Nitron II, H2SO4;

Reference yield:

methyl 3-formyl-cis-crotonate (153812-94-3) → C32H46N2O2S

Guidance literature:

Multi-step reaction with 11 steps

1: 61 percent / 120 h / 98 - 105 °C

2: 80 percent / potassium hexamethyldisilazide / toluene / 12 h / 25 °C

3: 99 percent / LiAlH₄ / diethyl ether / 0.5 h / 0 °C

4: 75 percent / o-nitrophenyl selenocyanate, tributylphosphine / tetrahydrofuran / 1 h / 25 °C

6: oxalyl chloride / benzene / 2 h / 23 °C

7: 80 percent / triethylamine / benzene / 5 h / 23 °C

9: 83 percent / H₂ / Pd/C / tetrahydrofuran; pyridine / 24 h / 23 °C / 760 Torr

10: 89 percent / NaOMe / methanol / -78 °C

11: ethanol / 12 h / 23 °C

With lithium aluminium tetrahydride; ortho-nitrophenyl selenocyanate; oxalyl dichloride; tributylphosphine; hydrogen; sodium methylate; potassium hexamethylsilazane; triethylamine; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; toluene; benzene;

DOI:10.1021/ja00300a049

upstream raw materials:

methyl 2-methyl-3-<(trimethylsilyl)oxy>-1-cyclopropanecarboxylate

Downstream raw materials:

(3E,5E,7E,9E,11E,13E,15E)-3,7,12,16-tetramethyl-18-[(4R)-2,6,6-trimethyl-4-triethylsilyloxycyclohex-1-en-1-yl]octadeca-3,5,7,9,11,13,15-heptaen-17-yn-2-one

Refernces