Production of 2,5-dihydrofurans and analogous compounds

US8404872B2 · kind B2 · utility

Assignee

• Cornell University · IT

Inventors

• Jon Njardarson · Tucson, US
• Lindsay Batory · Ithaca, US
• Matthew Brichacek · Little Falls, US
• Renato Alejandro Bauer · Indianapolis, US
• Erik Rogers · Saratoga Springs, US

Key dates

• Filing date: Mar 12, 2007
• Grant date: Mar 26, 2013
• Expiry date: Oct 22, 2027

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D493/08
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

Vinyl oxiranes are rearranged to 2,5-dihydrofuran using catalyst (III) or (IV). The 2,5-dihydrofuran can be reduced to tetrahydrofuran. 3,4-Epoxy-1-butene substrate is converted to 2,5-dihydrofuran which in turn is converted to tetrahydrofuran. Substrate for making 3-methyltetrahydrofuran is prepared from isoprene. Substrate for making 2-methyltetrahydrofuran is prepared from piperylene. Reactions analogous to that with vinyl oxiranes are carried out with vinyl thiiranes and vinyl aziridines.