3-Furoic acid → 3,4-Dihydro-2H-pyran-5-carboxylic acid

Participants

Reaction Steps

Tetrahydrofuran-3-carboxylic acid (formula I: n=1, X=S) can be prepared by hydrogenation of furan-3-carboxylic acid with Raney Nickel (Boekelheide and Morrison, J. Am. Chem. Soc. 80 (1958) 3905), tetrahydrothiophene-3-carboxylic acid (formula I: n=1, X=S) is accessible by reaction of methyl 1,4-dibromobutane-2-carboxylate with sodium sulfide and subsequent alkaline hydrolysis of the ester group (Kapovits and Kucsman, Acta Chim. Acad. Sci. Hung. 34 (1962) 79), (2H)-tetrahydropyran-3-carboxylic acid (formula I: n=2, X=S) can be obtained by hydrogenation of 2,3-dihydro-(4H)-pyran-5-carboxylic acid with Raney Nickel (Silberman, J. Org. Chem. 25 (1960) 151), (2H)-tetrahydrothiopyran-3-carboxylic acid (formula I: n=2, X=S) can be prepared, for example, from ethyl 1,5-dibromopentane-2-carboxylate by ring closure with sodium sulfide and subsequent alkaline hydrolysis (Kapovits and Kucsman, Acta Chim. Acad. Sci. Hung. 34 (1962) 79).

Provenance & Evidence