Ammonia → Methyl tetrahydrofuran-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a mixture of methyl tetrahydrofuran-2-carboxylic acid (11.6 g, 100 mmol), MeOH (20 mL), and toluene (30 mL) was slowly added concentrated H2SO4 (6 g). The resulting biphasic mixture was heated in a sealed pressure vessel for 1 hour at 95° C. The reaction was then cooled to 0° C. and 7N NH3 in MeOH was added until the pH reached between 7 and 9. Na2SO4 was then added, and the reaction was passed through short plug of silica gel, eluting with DCM. The resulting mixture was distilled at 64° C. under vacuum to afford the product as a clear liquid.

Provenance & Evidence