N-(4-oxo-4-phenylbutyl)acetamide

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Thiosemicarbazide (2.85 g, 31.3 mmol) was added to a solution of N-(4-oxo-4-phenyl-butyl)-acetamide (4.28 g, 20.9 mmol), prepared in the previous step, in 75 ml of methanol plus 5.6 ml of 1 N HCl, plus 5.6 ml of water and the reaction stirred at room temperature for 42 hours. The reaction was concentrated under reduced pressure to remove the methanol. The residue was partitioned between methylene chloride and water. The organic layer was separated, washed five times with water, dried (MgSO4) and the solvent removed under reduced pressure to give 4.77 g of a yellow solid Recrystallization of this solid from ethyl acetate gave the title compound (3.53 g, 61%) as an off-white solid, mp 74-83° C. The reaction was concentrated under reduced pressure to remove the methanol The residue was partitioned between methylene chloride and water The organic layer was separated washed five times with water dried (MgSO4) the solvent removed under reduced pressure to give 4.77 g of a yellow solid Recrystallization of this solid from ethyl acetate

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Pyridinium chlorochromate (10.08 g, 46.8 mmol) was added to a solution of N-(4-hydroxy-4-phenyl-butyl)-acetamide (6.46 g, 31.2 mmol), prepared in the previous step, in 200 ml of methylene chloride and the mixture stirred at room temperature for 1.5 hours. The entire reaction mixture was poured onto 200 g of silica gel (230-400 mesh) and the material eluted with ethyl acetate. Isolation of the major fraction gave N-(4-oxo-4-phenyl-butyl)-acetamide (4.35 g, 68%) as a light brown solid, mp 92-95° C. The entire reaction mixture was poured onto 200 g of silica gel (230-400 mesh) the material eluted with ethyl acetate