2,5-Dimethoxytetrahydrofuran → HCID 10354786, compound

Participants

Reaction Steps

To 100 ml of cooled (0° C.) acetic acid was added α-(2-fluorophenyl)benzenemethanamine (13.09 g). This mixture was then brought to room temperature and 2,5-dimethoxytetrahydrofuran (8.60 g) was added dropwise. The mixture was heated at reflux for 1.5 hours, after which time TLC (thin layer chromatography) showed absence of amine. The mixture was cooled and most of the acetic acid was removed by evaporation. The mixture was dissolved in ether and washed (3×H2O; 1×sat. NaHCO3), dried (sat. NaCl and anhydrous MgSO4), filtered and concentrated to yield a brown solid. Distillation (117° [email protected] mmHg) gave a slightly yellow solid (11.33 g). A sample was recrystallized from acetonitrile to give a white crystal, mp 81°-82.5° C.

Provenance & Evidence