4-propan-2-yloxycyclohexan-1-one

Conditions: temp:2.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Trimethylphosphonoacetate (700 mg, 3.87 mmol) was solved in 10 ml of THF and added into a cold (0-5° C.) mixture of sodium hydride (169 mg, 3.87 mmol, 55%) in 10 ml THF. After 1 hour stirring at 0-5° C. 4-isopropoxy-cyclohexanone (550 mg, 3.5 mmol) in 5 ml THF was added drop wise. The reaction mixture was quenched after 1 hour at room temperature with saturated NaHCO3-solution and extracted two times with ethyl acetate. The organic extracts were washed with brine, dried with sodium sulfate, filtered and evaporated. The crude product was purified with column chromatography on silica gel using heptane:ethyl acetate 90:10->20:80. The product fractions were concentrated to give 550 mg (74% yield) of a colorless liquid. MS (m/e): 213.3 (M+H+). The reaction mixture was quenched after 1 hour at room temperature with saturated NaHCO3-solution extracted two times with ethyl acetate The organic extracts were washed with brine dried with sodium sulfate filtered evaporated The crude product was purified with column chromatography on silica gel The product fractions were concentrated

Conditions: temp:2.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Trimethylphosphonoacetate (700 mg, 3.87 mmol) was solved in 10 ml of THF and added into a cold (0-5° C.) mixture of sodium hydride (169 mg, 3.87 mmol, 55%) in 10 ml THF. After 1 hour stirring at 0-5° C. 4-isopropoxy-cyclohexanone (550 mg, 3.5 mmol) in 5 ml THF was added drop wise. The reaction mixture was quenched after 1 hour at room temperature with saturated NaHCO3-solution and extracted two times with ethyl acetate. The organic extracts were washed with brine, dried with sodium sulfate, filtered and evaporated. The crude product was purified with column chromatography on silica gel using heptane:ethyl acetate 90:10->20:80. The product fractions were concentrated to give 550 mg (74% yield) of a colorless liquid. MS (m/e): 213.3 (M+H+). The reaction mixture was quenched after 1 hour at room temperature with saturated NaHCO3-solution extracted two times with ethyl acetate The organic extracts were washed with brine dried with sodium sulfate filtered evaporated The crude product was purified with column chromatography on silica gel The product fractions were concentrated

Conditions: temp:2.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Trimethylphosphonoacetate (700 mg, 3.87 mmol) was solved in 10 ml of THF and added into a cold (0-5° C.) mixture of sodium hydride (169 mg, 3.87 mmol, 55%) in 10 ml THF. After 1 hour stirring at 0-5° C. 4-isopropoxy-cyclohexanone (550 mg, 3.5 mmol) in 5 ml THF was added drop wise. The reaction mixture was quenched after 1 hour at room temperature with saturated NaHCO3-solution and extracted two times with ethyl acetate. The organic extracts were washed with brine, dried with sodium sulfate, filtered and evaporated. The crude product was purified with column chromatography on silica gel using heptane:ethyl acetate 90:10->20:80. The product fractions were concentrated to give 550 mg (74% yield) of a colorless liquid. MS (m/e): 213.3 (M+H+). The reaction mixture was quenched after 1 hour at room temperature with saturated NaHCO3-solution extracted two times with ethyl acetate The organic extracts were washed with brine dried with sodium sulfate filtered evaporated The crude product was purified with column chromatography on silica gel The product fractions were concentrated

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of 8-isopropoxy-1,4-dioxaspiro[4.5]decane (0.464 g, 2.317 mmol) in THF (2 mL) and water (2 mL), p-TsOH (0.080 g, 0.463 mmol) was added. The mixture was heated to 100° C. overnight. The resulting mixture was allowed to cool to room temperature and partitioned between EtOAc (30 mL) and water (30 mL). The organic phase was washed with brine (30 mL), dried over MgSO4 and filtered. The solvent was removed under reduced pressure to afford the title compound; to cool to room temperature partitioned between EtOAc (30 mL) and water (30 mL) The organic phase was washed with brine (30 mL) dried over MgSO4 filtered The solvent was removed under reduced pressure