5-(ethoxycarbonyl)furan-2-carboxylic acid synthesis

6synthesis methods

Product Name:5-(ethoxycarbonyl)furan-2-carboxylic acid
CAS Number:32933-01-0
Molecular formula:C8H8O5
Molecular Weight:184.15

53662-83-2 Synthesis

2,5-FURANDICARBOXYLIC ACID DIETHYL ESTER

53662-83-2
118 suppliers
$6.00/250mg

5-(ethoxycarbonyl)furan-2-carboxylic acid

32933-01-0
14 suppliers
$106.04/100mgs:

Yield:32933-01-0 95%

Reaction Conditions:

with sodium hydroxide in ethanol at 20; for 18 h;Inert atmosphere;

Steps:

Synthesis of 5-(ethoxycarbonyl)furan-2-carboxylic acid (18)

To a solution of the above furan (1.00 g, 4.71 mmol) in dry EtOH (10 mL) was added a solution of dry NaOH (226 mg, 5.65 mmol) in dry EtOH (2 mL) dropwise over 20 min, and the resulting solution stirred at ambient temperature under a nitrogen atmosphere for 18 h. The solution was concentrated in vacuo, the residue dissolved in water (10 mL) and washed with EtOAc (3x 10 mL). The solution was acidified to pH = 1 with 1M HCl and the resulting precipitate filtered, washed with water (3x 10 mL) and air dried to afford 18 as an off-white solid (824 mg, 95%). Experimental data as per literature. ADDIN EN.CITE Sigeru19711944194194017Torii SigeruTanaka HideoOgo Hitosi Yamasita Siro Anodic Reaction of 5-Alkyl-2-furoic Acids in Protic Solvents Bulletin of the Chemical Society of JapanBulletin of the Chemical Society of JapanBull. Chem. Soc. Jpn.1079-1084441971⁴ ¹H NMR (500 MHz, DMSO-d₆) δ1.36 (t, J = 7.0 Hz, 3H), 4.42 (q, J = 7.0 Hz, 2H), 7.22 (d, J = 3.6 Hz, 1H), 7.28 (d, J = 3.6 Hz, 1H). ¹³C NMR (125 MHz, DMSO-d₆) δ 14.5, 62.1, 117.6, 118.3, 147.5, 160.0.

References:

Schumann, Nicholas C.;Bruning, John;Marshall, Andrew C.;Abell, Andrew D. [Bioorganic and Medicinal Chemistry Letters,2019,vol. 29,# 3,p. 396 - 399] Location in patent:supporting information

3238-40-2 Synthesis