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Names | |
---|---|
Preferred IUPAC name
Oxolane-2-carboxylic acid | |
Other names
Tetrahydro-2-furoic acid; Tetrahydrofuran-2-carboxylic acid; Tetrahydrofuroic acid
| |
Identifiers | |
3D model (
JSmol)
|
|
ChEMBL | |
ChemSpider | |
DrugBank | |
ECHA InfoCard | 100.122.132 |
EC Number |
|
MeSH | C063698 |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
C5H8O3 | |
Molar mass | 116.116 g·mol−1 |
Appearance | colorless oil |
Density | 1.262 g/cm3 @ 20 °C |
Melting point | 21 °C (70 °F; 294 K) |
Boiling point | 135 °C (275 °F; 408 K) 20 mmHg |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
Tetrahydro-2-furoic acid is an organic compound with the formula HO2CC4H7O. It is a colorless oil. Tetrahydro-2-furoic acid is a useful pharmaceutical intermediate relevant to the production of several drugs, including Terazosin for the treatment of prostate enlargement and hypertension. [1] [2] or high boiling liquid, [3]
Furoic acid is reduced to tetrahydro-2-furoic acid, as originally reported in 1913 by Wienhaus. [4] Tetrahydro-2-furoic acid has been prepared via selective hydrogenation of 2-furoic acid over a bimetallic catalyst of palladium-nickel supported on alumina. [5]
Enantioselective heterogeneous hydrogenation of furoic acid to chiral tetrahydro-2-furoic acid proceeds in the presence of cinchonidine-modified alumina supported palladium catalyst in 95% yield and 32% enantiomeric excess. [6] Similarly, homogeneous hydrogenation to chiral tetrahydro-2-furoic acid proceeds quantitatively with 24-27% enantiomeric excess in methanol solution employing a chiral, ferrocene-phosphine catalyst. [7]
Reaction of tetrahydro-2-furoic acid with the hydrochloride salt of 3-[(4-amino-6,7-dimethoxy-2-quinazolinyl)methylamino]-propanenitrile provided alfuzosin, a drug for the treatment of benign prostatic hyperplasia (BPH). [8]
A key intermediate to faropenem, an antibiotic for the treatment of acute bacterial sinusitis, chronic bronchitis and pneumonia has been prepared from tetrahydro-2-furoic acid via a process including chiral resolution and chlorination. [9]
Tecadenoson is another example of a drug made using tetrahydro-2-furoic acid.
![]() | |
Names | |
---|---|
Preferred IUPAC name
Oxolane-2-carboxylic acid | |
Other names
Tetrahydro-2-furoic acid; Tetrahydrofuran-2-carboxylic acid; Tetrahydrofuroic acid
| |
Identifiers | |
3D model (
JSmol)
|
|
ChEMBL | |
ChemSpider | |
DrugBank | |
ECHA InfoCard | 100.122.132 |
EC Number |
|
MeSH | C063698 |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
Properties | |
C5H8O3 | |
Molar mass | 116.116 g·mol−1 |
Appearance | colorless oil |
Density | 1.262 g/cm3 @ 20 °C |
Melting point | 21 °C (70 °F; 294 K) |
Boiling point | 135 °C (275 °F; 408 K) 20 mmHg |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
Tetrahydro-2-furoic acid is an organic compound with the formula HO2CC4H7O. It is a colorless oil. Tetrahydro-2-furoic acid is a useful pharmaceutical intermediate relevant to the production of several drugs, including Terazosin for the treatment of prostate enlargement and hypertension. [1] [2] or high boiling liquid, [3]
Furoic acid is reduced to tetrahydro-2-furoic acid, as originally reported in 1913 by Wienhaus. [4] Tetrahydro-2-furoic acid has been prepared via selective hydrogenation of 2-furoic acid over a bimetallic catalyst of palladium-nickel supported on alumina. [5]
Enantioselective heterogeneous hydrogenation of furoic acid to chiral tetrahydro-2-furoic acid proceeds in the presence of cinchonidine-modified alumina supported palladium catalyst in 95% yield and 32% enantiomeric excess. [6] Similarly, homogeneous hydrogenation to chiral tetrahydro-2-furoic acid proceeds quantitatively with 24-27% enantiomeric excess in methanol solution employing a chiral, ferrocene-phosphine catalyst. [7]
Reaction of tetrahydro-2-furoic acid with the hydrochloride salt of 3-[(4-amino-6,7-dimethoxy-2-quinazolinyl)methylamino]-propanenitrile provided alfuzosin, a drug for the treatment of benign prostatic hyperplasia (BPH). [8]
A key intermediate to faropenem, an antibiotic for the treatment of acute bacterial sinusitis, chronic bronchitis and pneumonia has been prepared from tetrahydro-2-furoic acid via a process including chiral resolution and chlorination. [9]
Tecadenoson is another example of a drug made using tetrahydro-2-furoic acid.