Furan → HCID 13243429, compound

Participants

Reaction Steps

A stirred solution of 10.0 g (0.056 mol) of 3-amino-2-methylphenylmethyl acetate and 37.4 g (0.055 mol) of furan was heated to reflux, and 8.6 g (0.084 mol) of tert-butyl nitrite was added dropwise during 30 minutes. Upon complete addition, the reaction mixture was heated under reflux an additional 1.5 hours, then cooled, and 300 mL of heptane was added. The solution was filtered through 50 g of silica gel. The silica gel was washed with 400 mL of pentane. The wash and filtrate were combined and concentrated under reduced pressure to give a residual oil which was subjected to column chromatography on silica gel, eluting with toluene. The appropriate fractions were combined and concentrated under reduced pressure to give a residual oil. The oil was subjected to distillation under reduced pressure using a Kugelrohr distilling system to give 4.1 g of 3-(2-furanyl)-2-methylphenylmethyl acetate, b.p. 94±2° C./0.05 mm.

Provenance & Evidence