Ethyl 5-[(1,3-dioxoisoindol-2-yl)methyl]-2-oxooxolane-3-carboxylate

Base Information

• Chemical Name: Ethyl 5-[(1,3-dioxoisoindol-2-yl)methyl]-2-oxooxolane-3-carboxylate
• CAS No.: 6284-28-2
• Molecular Formula: C16H15NO6
• Molecular Weight: 317.298
• NSC Number: 7249
• DSSTox Substance ID: DTXSID401111557
• ChEMBL ID: CHEMBL2357767
• Mol file: 6284-28-2.mol

Synonyms:MLS002638001;6284-28-2;NSC7249;CHEMBL2357767;DTXSID401111557;HMS3093E24;NSC-7249;SMR001547506;3-Furancarboxylic acid, 5-[(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)methyl]tetrahydro-2-oxo-, ethyl ester

Chemical Property of Ethyl 5-[(1,3-dioxoisoindol-2-yl)methyl]-2-oxooxolane-3-carboxylate

Chemical Property:

• Vapor Pressure: 2.86E-10mmHg at 25°C
• Boiling Point: 503.6°C at 760 mmHg
• Flash Point: 258.4°C
• Density: 1.4g/cm³
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 317.08993720
• Heavy Atom Count: 23
• Complexity: 521

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1CC(OC1=O)CN2C(=O)C3=CC=CC=C3C2=O

Technology Process of Ethyl 5-[(1,3-dioxoisoindol-2-yl)methyl]-2-oxooxolane-3-carboxylate

There total 4 articles about Ethyl 5-[(1,3-dioxoisoindol-2-yl)methyl]-2-oxooxolane-3-carboxylate 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:

(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione (181140-34-1) + diethyl malonate (105-53-3) → 2-oxo-5-phthalimidomethyl-tetrahydro-furan-3-carboxylic acid ethyl ester (6284-28-2)

Guidance literature:

With sodium ethanolate; In tetrahydrofuran; ethanol; at 10 - 35 ℃; for 0.333333h; enantiospecific reaction; Inert atmosphere;

Reference yield:

phthalimide (136918-14-4,85-41-6) → 2-oxo-5-phthalimidomethyl-tetrahydro-furan-3-carboxylic acid ethyl ester (6284-28-2)

Guidance literature:

Multi-step reaction with 2 steps

1: aluminum oxide / 1-methyl-pyrrolidin-2-one / 64 - 68 °C

2: sodium ethanolate / ethanol; tetrahydrofuran / 0.33 h / 10 - 35 °C / Inert atmosphere

With aluminum oxide; sodium ethanolate; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; ethanol;

Reference yield:

2-(3-chloro-2-hydroxypropyl)-1H-isoindole-1,3(2H)-dione (19667-37-9,34839-11-7,148857-42-5,148857-44-7) → 2-oxo-5-phthalimidomethyl-tetrahydro-furan-3-carboxylic acid ethyl ester (6284-28-2)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate / toluene / Reflux

2: sodium ethanolate / ethanol; tetrahydrofuran / 0.33 h / 10 - 35 °C / Inert atmosphere

With sodium ethanolate; potassium carbonate; In tetrahydrofuran; ethanol; toluene;

upstream raw materials:

2-oxiranylmethylisoindole-1,3-dione

diethyl malonate

(-)-2-[(2R)-oxiran-2-ylmethyl]-1H-isoindole-1,3(2H)-dione

phthalimide

Downstream raw materials:

cis-1-acetyl-4-(toluene-4-sulfonyloxy)-DL-proline-methyl ester

cis-1-acetyl-4-(toluene-4-sulfonyloxy)-DL-proline

cis-1-acetyl-4-hydroxy-DL-proline

trans-4-hydroxy-D,L-proline