Ethyl Acetate → 2-{1-[(Benzyloxy)methyl]cyclobutyl}ethanethioamide

Participants

Reaction Steps

To a solution of 9.7 g (45 mmol) of {1-[(benzyloxy)methyl]cyclobutyl}acetonitrile in 100 mL of tetrahydrofuran and 10 mL of water was added 15.13 mL (90.2 mmol) of diethyldithiophosphate and the contents heated at reflux for 16 h. Ethyl acetate and water were added, and the layers separated. The organic phase was dried using magnesium sulfate and concentrated under vacuum to afford the crude product, which was purified by silica gel chromatography using ethyl acetate:hexane (2:8) as the eluent to afford 8.0 g (71%) of 2-{1-[(benzyloxy)methyl]cyclobutyl}ethanethioamide as a colorless oil. 1H NMR (300 MHz, CDCl3) δ 8.00 (br s, 2H), 7.39-7.30 (m, 5H), 4.59 (s, 2H), 3.58 (s, 2H), 3.09 (s, 2H), 2.14-1.87 (m, 6H).

Provenance & Evidence