ethyl 2-(1,4-dioxaspiro[4.5]decan-6-yl)acetate

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

実験手順: Under an argon atmosphere, a solution of (±)-6-(ethoxycarbonylmethyl)-1,4-dioxaspiro[4.5]decane (1.00 g, 4.39 mmol) in diethyl ether (22 ml) was cooled to 0° C. Lithium aluminium hydride (333 mg, 8.77 mmol) was added and the mixture was stirred at room temperature for 3 h. The mixture was cooled to 0° C., quenched with ethyl acetate (10 ml) and 2 M sodium hydroxide solution (50 ml). The mixture was extracted with chloroform (3×50 ml) and the combined organic extracts were dried over magnesium sulphate. The solvent was evaporated under reduced pressure to give the crude product which was purified using flash column chromatography with hexane-ethyl acetate (3:7) to give (±)-6-(2'-hydroxyethyl)-1,4-dioxaspiro[4.5]decane (767 mg, 94% yield) as a colourless oil. Rf 0.30 (hexane-ethyl acetate, 3:7). The mixture was cooled to 0° C. quenched with ethyl acetate (10 ml) and 2 M sodium hydroxide solution (50 ml) The mixture was extracted with chloroform (3×50 ml) the combined organic extracts were dried over magnesium sulphate The solvent was evaporated under reduced pressure to give the crude product which was purified

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

実験手順: Under an argon atmosphere, ethylene glycol (7.6 ml, 135.87 mmol) and para-toluenesulfonic acid (516 mg, 2.72 mmol) were added to a solution of (±)-2-(ethoxycarbonylmethyl)cyclohexanone (5.00 g, 27.17 mmol) in toluene (136 ml). The mixture was heated to reflux in a Dean Stark apparatus for 4 h and then allowed to cool to room temperature and quenched with sodium bicarbonate (5 g) and a saturated sodium bicarbonate solution (150 ml). The organic phase was separated from the aqueous phase which was extracted with ethyl acetate (3×100 ml). The combined organic phases were washed with a saturated sodium bicarbonate solution (100 ml) and brine (100 ml). The organic phase was dried over magnesium sulphate and the solvent was evaporated under reduced pressure to give the crude product which was purified using flash column chromatography with hexane-ethyl acetate (9:1) to give (±)-6-(ethoxycarbonylmethyl)-1,4-dioxaspiro[4.5]decane (4.59 g, 74% yield) as a colourless oil. Rf 0.18 (hexane-ethyl acetate, 9:1). The mixture was heated to reflux in a Dean Stark apparatus for 4 h quenched with sodium bicarbonate (5 g) The organic phase was separated from the aqueous phase which was extracted with ethyl acetate (3×100 ml) The combined organic phases were washed with a saturated sodium bicarbonate solution (100 ml) and brine (100 ml) The organic phase was dried over magnesium sulphate the solvent was evaporated under reduced pressure to give the crude product which was purified

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

実験手順: Under an argon atmosphere, a solution of (±)-6-(ethoxycarbonylmethyl)-1,4-dioxaspiro[4.5]decane (1.00 g, 4.39 mmol) in diethyl ether (22 ml) was cooled to 0° C. Lithium aluminium hydride (333 mg, 8.77 mmol) was added and the mixture was stirred at room temperature for 3 h. The mixture was cooled to 0° C., quenched with ethyl acetate (10 ml) and 2 M sodium hydroxide solution (50 ml). The mixture was extracted with chloroform (3×50 ml) and the combined organic extracts were dried over magnesium sulphate. The solvent was evaporated under reduced pressure to give the crude product which was purified using flash column chromatography with hexane-ethyl acetate (3:7) to give (±)-6-(2'-hydroxyethyl)-1,4-dioxaspiro[4.5]decane (767 mg, 94% yield) as a colourless oil. Rf 0.30 (hexane-ethyl acetate, 3:7). The mixture was cooled to 0° C. quenched with ethyl acetate (10 ml) and 2 M sodium hydroxide solution (50 ml) The mixture was extracted with chloroform (3×50 ml) the combined organic extracts were dried over magnesium sulphate The solvent was evaporated under reduced pressure to give the crude product which was purified

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

実験手順: Under an argon atmosphere, ethylene glycol (7.6 ml, 135.87 mmol) and para-toluenesulfonic acid (516 mg, 2.72 mmol) were added to a solution of (±)-2-(ethoxycarbonylmethyl)cyclohexanone (5.00 g, 27.17 mmol) in toluene (136 ml). The mixture was heated to reflux in a Dean Stark apparatus for 4 h and then allowed to cool to room temperature and quenched with sodium bicarbonate (5 g) and a saturated sodium bicarbonate solution (150 ml). The organic phase was separated from the aqueous phase which was extracted with ethyl acetate (3×100 ml). The combined organic phases were washed with a saturated sodium bicarbonate solution (100 ml) and brine (100 ml). The organic phase was dried over magnesium sulphate and the solvent was evaporated under reduced pressure to give the crude product which was purified using flash column chromatography with hexane-ethyl acetate (9:1) to give (±)-6-(ethoxycarbonylmethyl)-1,4-dioxaspiro[4.5]decane (4.59 g, 74% yield) as a colourless oil. Rf 0.18 (hexane-ethyl acetate, 9:1). The mixture was heated to reflux in a Dean Stark apparatus for 4 h quenched with sodium bicarbonate (5 g) The organic phase was separated from the aqueous phase which was extracted with ethyl acetate (3×100 ml) The combined organic phases were washed with a saturated sodium bicarbonate solution (100 ml) and brine (100 ml) The organic phase was dried over magnesium sulphate the solvent was evaporated under reduced pressure to give the crude product which was purified

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

実験手順: Under an argon atmosphere, ethylene glycol (7.6 ml, 135.87 mmol) and para-toluenesulfonic acid (516 mg, 2.72 mmol) were added to a solution of (±)-2-(ethoxycarbonylmethyl)cyclohexanone (5.00 g, 27.17 mmol) in toluene (136 ml). The mixture was heated to reflux in a Dean Stark apparatus for 4 h and then allowed to cool to room temperature and quenched with sodium bicarbonate (5 g) and a saturated sodium bicarbonate solution (150 ml). The organic phase was separated from the aqueous phase which was extracted with ethyl acetate (3×100 ml). The combined organic phases were washed with a saturated sodium bicarbonate solution (100 ml) and brine (100 ml). The organic phase was dried over magnesium sulphate and the solvent was evaporated under reduced pressure to give the crude product which was purified using flash column chromatography with hexane-ethyl acetate (9:1) to give (±)-6-(ethoxycarbonylmethyl)-1,4-dioxaspiro[4.5]decane (4.59 g, 74% yield) as a colourless oil. Rf 0.18 (hexane-ethyl acetate, 9:1). The mixture was heated to reflux in a Dean Stark apparatus for 4 h quenched with sodium bicarbonate (5 g) The organic phase was separated from the aqueous phase which was extracted with ethyl acetate (3×100 ml) The combined organic phases were washed with a saturated sodium bicarbonate solution (100 ml) and brine (100 ml) The organic phase was dried over magnesium sulphate the solvent was evaporated under reduced pressure to give the crude product which was purified

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

実験手順: Under an argon atmosphere, a solution of (±)-6-(ethoxycarbonylmethyl)-1,4-dioxaspiro[4.5]decane (1.00 g, 4.39 mmol) in diethyl ether (22 ml) was cooled to 0° C. Lithium aluminium hydride (333 mg, 8.77 mmol) was added and the mixture was stirred at room temperature for 3 h. The mixture was cooled to 0° C., quenched with ethyl acetate (10 ml) and 2 M sodium hydroxide solution (50 ml). The mixture was extracted with chloroform (3×50 ml) and the combined organic extracts were dried over magnesium sulphate. The solvent was evaporated under reduced pressure to give the crude product which was purified using flash column chromatography with hexane-ethyl acetate (3:7) to give (±)-6-(2'-hydroxyethyl)-1,4-dioxaspiro[4.5]decane (767 mg, 94% yield) as a colourless oil. Rf 0.30 (hexane-ethyl acetate, 3:7). The mixture was cooled to 0° C. quenched with ethyl acetate (10 ml) and 2 M sodium hydroxide solution (50 ml) The mixture was extracted with chloroform (3×50 ml) the combined organic extracts were dried over magnesium sulphate The solvent was evaporated under reduced pressure to give the crude product which was purified

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

実験手順: Under an argon atmosphere, ethylene glycol (7.6 ml, 135.87 mmol) and para-toluenesulfonic acid (516 mg, 2.72 mmol) were added to a solution of (±)-2-(ethoxycarbonylmethyl)cyclohexanone (5.00 g, 27.17 mmol) in toluene (136 ml). The mixture was heated to reflux in a Dean Stark apparatus for 4 h and then allowed to cool to room temperature and quenched with sodium bicarbonate (5 g) and a saturated sodium bicarbonate solution (150 ml). The organic phase was separated from the aqueous phase which was extracted with ethyl acetate (3×100 ml). The combined organic phases were washed with a saturated sodium bicarbonate solution (100 ml) and brine (100 ml). The organic phase was dried over magnesium sulphate and the solvent was evaporated under reduced pressure to give the crude product which was purified using flash column chromatography with hexane-ethyl acetate (9:1) to give (±)-6-(ethoxycarbonylmethyl)-1,4-dioxaspiro[4.5]decane (4.59 g, 74% yield) as a colourless oil. Rf 0.18 (hexane-ethyl acetate, 9:1). The mixture was heated to reflux in a Dean Stark apparatus for 4 h quenched with sodium bicarbonate (5 g) The organic phase was separated from the aqueous phase which was extracted with ethyl acetate (3×100 ml) The combined organic phases were washed with a saturated sodium bicarbonate solution (100 ml) and brine (100 ml) The organic phase was dried over magnesium sulphate the solvent was evaporated under reduced pressure to give the crude product which was purified