4,4-dichlorocyclohexan-1-one

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

実験手順: To a solution of 8,8-dichloro-1,4-dioxaspiro[4.5]decane (0.27 g, 1.28 mmol) in acetone (3.5 mL), aqueous 2N hydrochloric acid (5 mL) was added and the reaction mixture was stirred at room temperature overnight, diluted with water and extracted twice with diethyl ether. The combined organic phases were washed with water, brine, dried over sodium sulfate and evaporated to dryness. The resulting crude 4,4-dichlorocyclohexanone, obtained as a white solid, was used in the next steps without any further purification (0.17 g, 78% yield). extracted twice with diethyl ether The combined organic phases were washed with water, brine dried over sodium sulfate evaporated to dryness

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

実験手順: To a solution of 8,8-dichloro-1,4-dioxaspiro[4.5]decane (0.27 g, 1.28 mmol) in acetone (3.5 mL), aqueous 2N hydrochloric acid (5 mL) was added and the reaction mixture was stirred at room temperature overnight, diluted with water and extracted twice with diethyl ether. The combined organic phases were washed with water, brine, dried over sodium sulfate and evaporated to dryness. The resulting crude 4,4-dichlorocyclohexanone, obtained as a white solid, was used in the next steps without any further purification (0.17 g, 78% yield). extracted twice with diethyl ether The combined organic phases were washed with water, brine dried over sodium sulfate evaporated to dryness

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

実験手順: To a solution of 8,8-dichloro-1,4-dioxaspiro[4.5]decane (0.27 g, 1.28 mmol) in acetone (3.5 mL), aqueous 2N hydrochloric acid (5 mL) was added and the reaction mixture was stirred at room temperature overnight, diluted with water and extracted twice with diethyl ether. The combined organic phases were washed with water, brine, dried over sodium sulfate and evaporated to dryness. The resulting crude 4,4-dichlorocyclohexanone, obtained as a white solid, was used in the next steps without any further purification (0.17 g, 78% yield). extracted twice with diethyl ether The combined organic phases were washed with water, brine dried over sodium sulfate evaporated to dryness

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

実験手順: To a mixture of 4,4-dichlorocyclohexanone (WO2011/006794A 1) (5.20 g, 31.10 mmol) in anhydrous methanol (100 mL) was added sodium borohydride (2.35 g, 62.20 mmol) at 0° C. The reaction mixture was allowed to warm to ambient temperature and stirred for 1 hour. Concentration in vacuo yielded a residue which was re-dissolved in methanol (50 mL) and concentrated again in vacuo. The residue was then purified by silica gel column chromatography using 10-100% ethyl acetate in hexanes as eluent to afford 4,4-dichlorocyclohexanol as an orange solid (1.90 g, 36%). Concentration in vacuo yielded a residue which concentrated again in vacuo The residue was then purified by silica gel column chromatography

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

実験手順: To a solution of 8,8-dichloro-1,4-dioxaspiro[4.5]decane (0.27 g, 1.28 mmol) in acetone (3.5 mL), aqueous 2N hydrochloric acid (5 mL) was added and the reaction mixture was stirred at room temperature overnight, diluted with water and extracted twice with diethyl ether. The combined organic phases were washed with water, brine, dried over sodium sulfate and evaporated to dryness. The resulting crude 4,4-dichlorocyclohexanone, obtained as a white solid, was used in the next steps without any further purification (0.17 g, 78% yield). extracted twice with diethyl ether The combined organic phases were washed with water, brine dried over sodium sulfate evaporated to dryness