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Tetrahydro-2-furoic acid : ウィキペディア英語版 | Tetrahydro-2-furoic acid
Tetrahydro-2-furoic acid is a low melting solid〔Franco Codignola and Mario Piacenza, "A process for the production of polyurethane resins", Italian Patent (1947), ES179144 (A1).〕 or high boiling liquid, depending on temperature. Tetrahydro-2-furoic acid is a useful pharmaceutical intermediate and is used in the process to several drugs, including Terazosin for the treatment of prostate enlargement and hypertension.〔Wen-Chih Chou, Ming-Chen Chou, Yann-Yu Lu and Shyh-Fong Chen, "Preparation of N-acylalkylenediamines as precursors of antihypertensive quinazolines", US Patent (2001), 6313293(B1).〕 == Synthesis ==
Furoic acid was reduced to tetrahydro-2-furoic acid in 1913 by Wienhaus. More recently, tetrahydro-2-furoic acid has been prepared via selective hydrogenation of 2-furoic acid over a bimetallic catalyst of palladium-nickel supported on alumina. Enantioselective heterogeneous hydrogenation of furoic acid to chiral tetrahydro-2-furoic acid was achieved in the presence of cinchonidine-modified alumina supported palladium catalyst in 95% yield and 32% enantiomeric excess. Similarly, homogeneous hydrogenation to chiral tetrahydro-2-furoic acid was accomplished in 100% yield and 24-27% enantiomeric excess in methanol solution employing a chiral, phosphine modified ferrocene catalyst.
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