5-(Ethoxycarbonyl)furan-2-boronic acid,pinacol ester

Base Information

• Chemical Name: 5-(Ethoxycarbonyl)furan-2-boronic acid,pinacol ester
• CAS No.: 1073338-92-7
• Molecular Formula: C13H21BO6
• Molecular Weight: 284
• Hs Code.: 2934999090
• Mol file: 1073338-92-7.mol

Synonyms:5-(Ethoxycarbonyl)furan-2-boronic acid,pinacol ester;2-(Ethoxycarbonyl)furan-5-boronic acid pinacol ester, 96%;Ethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan-2-carboxylate

Chemical Property of 5-(Ethoxycarbonyl)furan-2-boronic acid,pinacol ester

Chemical Property:

• Boiling Point: 364.0±27.0 °C(Predicted)
• PSA: 57.90000
• Density: 1.11±0.1 g/cm3(Predicted)
• LogP: 1.75550
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C

Purity/Quality:

97% ^*data from raw suppliers

5-(Ethoxycarbonyl)furan-2-boronicAcidPinacolEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 5-(Ethoxycarbonyl)furan-2-boronic acid, pinacol ester

Technology Process of 5-(Ethoxycarbonyl)furan-2-boronic acid,pinacol ester

There total 2 articles about 5-(Ethoxycarbonyl)furan-2-boronic acid,pinacol ester 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: 90.0%

Ethyl 2-furoate (614-99-3) + bis(pinacol)diborane (73183-34-3) → ethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan-2-carboxylate (1073338-92-7)

Guidance literature:

bis(pinacol)diborane; With 5-methyl-2-(thiophen-3-yl)pyridine; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; In tetrahydrofuran; at 20 ℃; for 0.0333333h; Inert atmosphere; Glovebox;

Ethyl 2-furoate; In tetrahydrofuran; at 80 ℃; for 12h; regioselective reaction; Inert atmosphere; Sealed tube;

DOI:10.1021/jacs.0c13415

Reference yield:

2-furanoic acid (88-14-2) → ethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan-2-carboxylate (1073338-92-7)

Guidance literature:

Multi-step reaction with 2 steps

1: sulfuric acid / 12 h / 100 °C / Sealed tube

2: 8-([2,2'-bipyridin]-5-yl)quinolin-2(1H)-one; potassium tert-butylate; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer / tetrahydrofuran / 12 h / 80 °C / Glovebox; Sealed tube

With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; sulfuric acid; 8-([2,2'-bipyridin]-5-yl)quinolin-2(1H)-one; potassium tert-butylate; In tetrahydrofuran;

DOI:10.1021/jacs.7b04490

Reference yield: 39.0%

ethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan-2-carboxylate (1073338-92-7) + C15H13ClF3NSSi (1224867-21-3) → C22H20F3NO3SSi (1224867-30-4)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tripotassium phosphate "n" hydrate; XPhos; In tert-butyl alcohol; at 70 ℃; for 6h; Inert atmosphere;

DOI:10.3987/COM-09-S(S)135

upstream raw materials:

Ethyl 2-furoate

bis(pinacol)diborane

2-furanoic acid

Downstream raw materials:

C₂₂H₂₀F₃NO₃SSi

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