Methyl 5-(2-methoxy-2-oxoethyl)furan-2-carboxylate

Base Information

• Chemical Name: Methyl 5-(2-methoxy-2-oxoethyl)furan-2-carboxylate
• CAS No.: 1087784-37-9
• Molecular Formula: C₉H₁₀O₅
• Molecular Weight: 198.175
• DSSTox Substance ID: DTXSID701271968
• Mol file: 1087784-37-9.mol

Synonyms:methyl 5-(2-methoxy-2-oxoethyl)furan-2-carboxylate;1087784-37-9;5-methoxycarbonylmethyl-furan-2-carboxylic acid methyl ester;SCHEMBL2707440;YWTRYDAONUXRNP-UHFFFAOYSA-N;DTXSID701271968;AKOS033183708;Methyl 5-(methoxycarbonyl)-2-furanacetate;CS-0247738;EN300-37300;G24603;methyl5-(2-methoxy-2-oxoethyl)furan-2-carboxylate;Z381338108

Chemical Property of Methyl 5-(2-methoxy-2-oxoethyl)furan-2-carboxylate

Chemical Property:

• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 198.05282342
• Heavy Atom Count: 14
• Complexity: 225

Purity/Quality:

99% ^*data from raw suppliers

Methyl5-(2-Methoxy-2-oxoethyl)furan-2-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC(=O)CC1=CC=C(O1)C(=O)OC

Technology Process of Methyl 5-(2-methoxy-2-oxoethyl)furan-2-carboxylate

There total 1 articles about Methyl 5-(2-methoxy-2-oxoethyl)furan-2-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: 44.0%

furfurylacetate (623-17-6) + carbon dioxide (124-38-9,18923-20-1) + diazomethyl-trimethyl-silane (18107-18-1) → 5-methoxycarbonylmethyl-furan-2-carboxylic acid methyl ester (1087784-37-9) + methyl 3-methoxycarbonylfuran-2-ylacetate (162337-80-6)

Guidance literature:

furfurylacetate; carbon dioxide; With bis(tributylphosphine)dichloropalladium(II); diethylzinc; In hexane; N,N-dimethyl-formamide; at 0 - 40 ℃; for 18h; under 760.051 Torr; Inert atmosphere;

diazomethyl-trimethyl-silane; In methanol; diethyl ether; for 0.166667h; Solvent; Temperature; Inert atmosphere;

DOI:10.1055/s-0037-1612414

Reference yield:

5-methoxycarbonylmethyl-furan-2-carboxylic acid methyl ester (1087784-37-9) → 5-[((1S,3R)-1-biphenyl-4-ylmethyl-3-carboxybutylcarbamoyl)methyl]furan-2-carboxylic acid (1257265-87-4) + (2R,4S)-5-biphenyl-4-yl-4-[(5-carboxymethylfuran-2-carbonyl)amino]-2-methylpentanoic acid (1257265-86-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydroxide / methanol / 18 h / 20 °C

2.1: triethylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 18 h / 20 °C

2.2: 5 h / 50 °C

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; sodium hydroxide; In methanol; N,N-dimethyl-formamide;

upstream raw materials:

furfurylacetate

carbon dioxide

diazomethyl-trimethyl-silane

Downstream raw materials:

5-[((1S,3R)-1-biphenyl-4-ylmethyl-3-carboxybutylcarbamoyl)methyl]furan-2-carboxylic acid

(2R,4S)-5-biphenyl-4-yl-4-[(5-carboxymethylfuran-2-carbonyl)amino]-2-methylpentanoic acid