Reactions of 2,2′,5′,2′-terfuran

Autor: J. D. Lehmkuhler, D. C. Myers, J. W. Mcfarland, B. M. Howe
Rok vydání: 1995
Předmět:
Zdroj: Journal of Heterocyclic Chemistry. 32:1747-1750
ISSN: 1943-5193
0022-152X
Popis: Formylation of 2,2′,5′,2′-terfuran (1) with N-methylformanilide and phosphorus oxychloride gave 5-formyl-2,2′,5′,2′-terfuran (2) and 5,5′-diformyl-2,2′5′,2′-terfuran (3). Reduction of 2 and 3 afforded 5-hydroxymethyl-2,2′,5′,2′-terfuran (4) and 5,5′ dihydroxymethyl-2,2′,5′,2′-terfuran (5), respectively. Terfuran 1 reacted with phenylmagnesium bromide to give 5-(phenylhydroxymethyl)-2,2′,5′,2′-terfuran (6), and was carbonated to 5-carboxy 2,2′,5′,2′-terfuran (7) and 5,5′-dicarboxy-2,2′,5′,2′-terfuran (8). Bromination of 1 with N-bromosuccinimide gave 5,5′-dibromo 2,2′,5′,2′-terfuran (9).
Databáze: OpenAIRE
Externí odkaz: