Ammonium Chloride → HCID 12532948, compound

Participants

Reaction Steps

To a solution of 2-bromobenzyl alcohol (7.8 g, 42 mmol) in tetrahydrofuran (80 ml) was added dropwise a 2.8 M solution of ethylmagnesium chloride in tetrahydrofuran (15 ml, 42 mmol). The reaction was exothermic, and the rate of addition was adjusted to maintain a gentle reflux. After completed addition magnesium turnings (1.0 g, 42 mmol) were added in portions. The mixture was heated at reflux for 2 h before addition of a solution of 1-benzyl-azepan-4-one (8.5 g, 42 mmol) in tetrahydrofuran (40 ml). The reaction mixture was heated for another 4 h at reflux. Cooling to room temperature was followed by slow addition of saturated ammonium chloride solution (50 ml), water (100 ml) and ethyl acetate (300 ml). The layers were separated, and the organic layer was concentrated to give a green oil. Flash column chromatography using a 2:1 mixture of heptane and ethyl acetate as eluent gave the title compound as a light yellow oil (8.0 g, 61%).

Provenance & Evidence