Ammonium Acetate → 4,5,6,7-Tetrahydro-1-benzofuran-4-amine

Participants

Reaction Steps

To a solution of 6,7-dihydro-1-benzofuran-4(5H)-one (2.0 g) in methanol (50 ml) was added 3 Å sieves (15 g), ammonium acetate (11.3 g) and sodium cyanoborohydride (1.22 g). After 48 h of stirring, the reaction mixture was filtered through celite, concentrated, dissolved in 1 N HCl (100 ml) and washed with ethyl ether (3×100 ml). The Aqueous layer was basified to pH 10 (NaOH), extracted methylene chloride (3×100 ml), dried MgSO4, filtered and concentrated to yield (760 mg, 38%) of the title compound as an oil:

Provenance & Evidence