2-METHOXY-3-METHOXYCARBONYL-5-PHENYL-FURAN

Base Information

• Chemical Name: 2-METHOXY-3-METHOXYCARBONYL-5-PHENYL-FURAN
• CAS No.: 115852-13-6
• Molecular Formula: C13H12 O4
• Molecular Weight: 232.236
• Mol file: 115852-13-6.mol

Synonyms:2-METHOXY-3-METHOXYCARBONYL-5-PHENYL-FURAN;2-METHYOXY-3-METHOXYCARBONYL-5-PHENYL-FURAN

Chemical Property of 2-METHOXY-3-METHOXYCARBONYL-5-PHENYL-FURAN

Chemical Property:

• Vapor Pressure: 4.1E-05mmHg at 25°C
• Melting Point: 79-80 °C(Solv: ligroine (8032-32-4); ethyl ether (60-29-7))
• Refractive Index: 1.529
• Boiling Point: 351.5°C at 760 mmHg
• Flash Point: 166.4°C
• PSA: 48.67000
• Density: 1.164g/cm³
• LogP: 2.74180

Purity/Quality:

99%min ^*data from raw suppliers

2-METHOXY-3-METHOXYCARBONYL-5-PHENYL-FURAN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-METHOXY-3-METHOXYCARBONYL-5-PHENYL-FURAN

There total 5 articles about 2-METHOXY-3-METHOXYCARBONYL-5-PHENYL-FURAN 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: 91.0%

dimethyl diazomalonate (6773-29-1) + phenylacetylene (536-74-3) → methyl 2-methoxy-5-phenyl-furan-3-carboxylate (115852-13-6)

Guidance literature:

With [Co(3,5-Di^tBu-IbuPhyrin)]; In 1,2-dichloro-benzene; at 80 ℃; for 24h; Temperature; regioselective reaction; Inert atmosphere;

DOI:10.1021/ja309446n

Reference yield: 89.0%

dimethyl 2-phenyl-cycloprop-2-ene-1,1-dicarboxylic ester (170751-24-3) → methyl 2-methoxy-5-phenyl-furan-3-carboxylate (115852-13-6)

Guidance literature:

With tris(triphenylphosphine)ruthenium(II) chloride; In tetrahydrofuran; at 20 ℃; for 11h; regioselective reaction; Inert atmosphere;

DOI:10.1002/asia.201000324

Reference yield: 63.0%

bis(methoxycarbonyl)(phenyliodinio)methanide (145838-86-4) + phenylacetylene (536-74-3) → methyl 2-methoxy-5-phenyl-furan-3-carboxylate (115852-13-6) + dimethyl 2-phenyl-cycloprop-2-ene-1,1-dicarboxylic ester (170751-24-3)

Guidance literature:

With dirhodium tetraacetate; at 110 ℃; for 0.0333333h;

DOI:10.1016/S0040-4039(02)01260-1

upstream raw materials:

2-phenyl-4-methyl-5-methoxyoxazole

propynoic acid methyl ester

bis(methoxycarbonyl)(phenyliodinio)methanide

phenylacetylene

Downstream raw materials:

methyl 4-hydroperoxy-4-methoxy-2-methoxycarbonyl-4-phenylbut-2-enoate

methyl 2-carbomethoxy-4-methylphenyl-4-oxo-2-butenoate

3-Benzoyl-oxirane-2,2-dicarboxylic acid dimethyl ester

methyl 1-methoxy-5-phenyl-2,3,7-trioxabicyclo<2.2.1>hept-5-ene-6-carboxylate

Refernces

• 1、 Chen, Jie,Ni, Shengjun,Ma, Shengming. "Highly regioselective synthesis of 2,3,5-trisubstituted furans via phosphine-catalyzed ring-opening cycloisomerization reactions of cyclopropenyl dicarboxylates". supporting information; experimental part. p. 931 - 934. Retrieved 2011/06/17.
• 2、 Ma, Shengming,Lu, Lianghua,Lu, Ping. "I--catalyzed methyl-oxygen bond cleavage in 2-methoxyfurans. An efficient synthesis of butenolides". . p. 1063 - 1065. Retrieved 2007/10/03.