5-phenylmethoxypentan-2-one

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Sodium borohydride (236 mg) was added to a mixed solution of 5-benzyloxy-2-pentanone (1.09 g, 5.67 mmol) in methanol (50 mL) in an ice bath, followed by stirring. After completion of the reaction, water was added to the reaction solution in an ice bath, and methanol was evaporated. The pH was adjusted to 4 with 2 mol/L hydrochloric acid. After extraction with chloroform-water, the organic layer was washed with a saturated sodium chloride solution and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1) to obtain 957 mg of the title compound (yield: 87%) as a colorless solid. was added to the reaction solution in an ice bath methanol was evaporated After extraction with chloroform-water the organic layer was washed with a saturated sodium chloride solution concentrated under reduced pressure The residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Benzyl trichloroacetimidate (1.85 g) was added to a mixed solution of 5-hydroxy-2-pentanone (500 mg, 4.89 mmol) in dichloromethane (20 mL) in an argon atmosphere at room temperature, and then trifluoromethanesulfonic acid (87 μL) was added in an ice bath. The mixture was returned to room temperature and stirred overnight. After completion of the reaction, a saturated sodium bicarbonate solution was added to the reaction solution in an ace bath, and the pH was adjusted to 8. After extraction with chloroform-water, the organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to obtain 610 mg of the title compound (yield: 65%) as a pale yellow oil. was returned to room temperature After completion of the reaction After extraction with chloroform-water the organic layer was concentrated under reduced pressure The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)