Diethyl 4-methylidene-5-oxooxolane-3,3-dicarboxylate

Base Information

• Chemical Name: Diethyl 4-methylidene-5-oxooxolane-3,3-dicarboxylate
• CAS No.: 56643-56-2
• Molecular Formula: C11H14O6
• Molecular Weight: 242.2253
• NSC Number: 126873
• DSSTox Substance ID: DTXSID20298907
• Wikidata: Q82041015
• ChEMBL ID: CHEMBL2181114
• Mol file: 56643-56-2.mol

Synonyms:56643-56-2;CHEMBL2181114;diethyl 4-methylidene-5-oxooxolane-3,3-dicarboxylate;NSC126873;DTXSID20298907;BDBM50398033;NSC-126873;3, dihydro-4-methylene-5-oxo-, diethyl ester

Chemical Property of Diethyl 4-methylidene-5-oxooxolane-3,3-dicarboxylate

Chemical Property:

• Vapor Pressure: 7.67E-05mmHg at 25°C
• Boiling Point: 342.2°Cat760mmHg
• Flash Point: 150.6°C
• Density: 1.22g/cm³
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 242.07903816
• Heavy Atom Count: 17
• Complexity: 352

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1(COC(=O)C1=C)C(=O)OCC

Technology Process of Diethyl 4-methylidene-5-oxooxolane-3,3-dicarboxylate

There total 5 articles about Diethyl 4-methylidene-5-oxooxolane-3,3-dicarboxylate 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:

tetraethyl ethane-1,1,2,2-tetracarboxylate (632-56-4) → diethyl α-methylene-γ-butyrolactone-β-dicarboxylate (56643-56-2)

Guidance literature:

Multi-step reaction with 2 steps

1: Na / ethanol / 2 h / 55 °C

2: conc HCl / 3 h / Heating

With hydrogenchloride; sodium; In ethanol;

DOI:10.1016/S0968-0896(01)00260-7

Reference yield:

diethyl 2-ethoxycarbonyl-3-methylbutadienoate (30313-07-6) → diethyl α-methylene-γ-butyrolactone-β-dicarboxylate (56643-56-2)

Guidance literature:

Multi-step reaction with 2 steps

1: LiAlH₄, cc. HCl / benzene / 1.) ice-water bath, 30 min 2.) RT, 2.5 h 2.) 0 deg C, 5 min

2: 30.5 g / KHCO₃ / 0.42 h / 65 °C

With hydrogenchloride; lithium aluminium tetrahydride; potassium hydrogencarbonate; In benzene;

DOI:10.1016/S0040-4020(01)82432-7

Reference yield:

formaldehyd (50-00-0,30525-89-4,61233-19-0) + triethyl prop-2-ene-1,1,2-tricarboxylate (71195-11-4) → diethyl α-methylene-γ-butyrolactone-β-dicarboxylate (56643-56-2)

Guidance literature:

With potassium hydrogencarbonate; at 65 ℃; for 0.416667h;

DOI:10.1016/S0040-4020(01)82432-7

upstream raw materials:

formaldehyd

triethyl prop-2-ene-1,1,2-tricarboxylate

α-Hydroxymethyl-α,β-bis-ethoxycarbonyl-paraconsaeureethylester

tetraethyl ethane-1,1,2,2-tetracarboxylate

Downstream raw materials:

α-methylene-γ-butyrolactone-β-carboxylic acid