8-(2-iodoethyl)-1,4-dioxaspiro[4.5]decane

反応条件: temp:3.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 233.0 g of the compound (21) and 800 mL of DMF were added to a reactor under nitrogen atmosphere, and stirred at 3° C. under cooling with ice. 92.9 g of potassium t-butoxide (t-BuOK) was added thereto by dividing into 10 portions at a temperature range of from 3 to 10° C. over 2 hours, followed by further stirring at 0° C. for 3 hours. After confirming that the reaction had been completed by GC analysis, the reaction mixture was poured into and mixed with a mixture of 1,500 mL of heptane and 1,500 mL of water at 0° C. The mixture was separated into an organic layer and an aqueous layer by standing still, so as to attain extraction to the organic layer. The resulting organic layer was fractionated and washed with water, followed by drying over anhydrous magnesium sulfate. The resulting organic layer was purified by silica gel column chromatography using heptane as eluent, and the solvent was removed by distillation under reduced pressure. The resulting residue was distilled under reduced pressure to obtain 103.3 g of 8-vinyl-1,4-dioxaspiro[4,5]decane (22) as a colorless transparent liquid. under cooling with ice by further stirring at 0° C. for 3 hours the reaction mixture was poured into and The mixture was separated into an organic layer extraction to the organic layer washed with water by drying over anhydrous magnesium sulfate The resulting organic layer was purified by silica gel column chromatography the solvent was removed by distillation under reduced pressure The resulting residue was distilled under reduced pressure

反応条件: temp:3.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 233.0 g of the compound (21) and 800 mL of DMF were added to a reactor under nitrogen atmosphere, and stirred at 3° C. under cooling with ice. 92.9 g of potassium t-butoxide (t-BuOK) was added thereto by dividing into 10 portions at a temperature range of from 3 to 10° C. over 2 hours, followed by further stirring at 0° C. for 3 hours. After confirming that the reaction had been completed by GC analysis, the reaction mixture was poured into and mixed with a mixture of 1,500 mL of heptane and 1,500 mL of water at 0° C. The mixture was separated into an organic layer and an aqueous layer by standing still, so as to attain extraction to the organic layer. The resulting organic layer was fractionated and washed with water, followed by drying over anhydrous magnesium sulfate. The resulting organic layer was purified by silica gel column chromatography using heptane as eluent, and the solvent was removed by distillation under reduced pressure. The resulting residue was distilled under reduced pressure to obtain 103.3 g of 8-vinyl-1,4-dioxaspiro[4,5]decane (22) as a colorless transparent liquid. under cooling with ice by further stirring at 0° C. for 3 hours the reaction mixture was poured into and The mixture was separated into an organic layer extraction to the organic layer washed with water by drying over anhydrous magnesium sulfate The resulting organic layer was purified by silica gel column chromatography the solvent was removed by distillation under reduced pressure The resulting residue was distilled under reduced pressure

反応条件: temp:3.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Fifth Step: 223.0 g of the compound (14) and 800 mL of DMF were added to a reactor under nitrogen atmosphere, and stirred at 3° C. under cooling with ice. 92.9 g of potassium t-butoxide (t-BuOK) was added thereto by dividing into 10 portions at a temperature range of from 3 to 10° C., followed by further stirring at 0° C. for 3 hours. After confirming that the reaction had been completed by GC analysis, the reaction mixture was poured into and mixed with a mixture of 1,500 mL of heptane and 1,500 mL of water at 0° C. The mixture was separated into an organic layer and an aqueous layer by standing still, so as to attain extraction to the organic layer. The resulting organic layer was fractionated and washed with water, followed by drying over anhydrous magnesium sulfate. The resulting organic layer was purified by silica gel column chromatography using heptane as eluent, and the solvent was removed by distillation under reduced pressure. The resulting residue was distilled under reduced pressure to obtain 103.3 g of 8-vinyl-1,4-dioxaspiro[4,5]decane (15) as a colorless transparent liquid. under cooling with ice by dividing into 10 portions at a temperature range of from 3 to 10° C. by further stirring at 0° C. for 3 hours the reaction mixture was poured into and The mixture was separated into an organic layer extraction to the organic layer washed with water by drying over anhydrous magnesium sulfate The resulting organic layer was purified by silica gel column chromatography the solvent was removed by distillation under reduced pressure The resulting residue was distilled under reduced pressure

反応条件: temp:3.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Fourth Step: 150.0 g of the compound (13), 274.3 g of triphenylphosphine (Ph3P), 71.3 g of imidazole and 900 mL of toluene were added to a reactor under nitrogen atmosphere, and stirred at 3° C. 255.5 g of iodine was added thereto by dividing into 10 portions at a temperature range of from 3 to 10° C., followed by further stirring at 0° C. for 3 hours. After confirming that the reaction had been completed by GC analysis, a yellow solid thus deposited was filtered off. The filtrate was concentrated, and 400 mL of heptane was added to the resulting residue, followed by filtering off a pale yellow solid thus deposited. The filtrate was concentrated, and the resulting residue was purified by silica gel column chromatography using toluene as eluent, and the solvent was removed by distillation under reduced pressure to obtain 223.9 g of 8-(2-iodoethyl)-1,4-dioxaspiro[4,5]decane (14) as a colorless transparent liquid. by dividing into 10 portions at a temperature range of from 3 to 10° C. by further stirring at 0° C. for 3 hours a yellow solid thus deposited was filtered off The filtrate was concentrated 400 mL of heptane was added to the resulting residue by filtering off a pale yellow solid The filtrate was concentrated the resulting residue was purified by silica gel column chromatography the solvent was removed by distillation under reduced pressure

反応条件: temp:3.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 233.0 g of the compound (21) and 800 mL of DMF were added to a reactor under nitrogen atmosphere, and stirred at 3° C. under cooling with ice. 92.9 g of potassium t-butoxide (t-BuOK) was added thereto by dividing into 10 portions at a temperature range of from 3 to 10° C. over 2 hours, followed by further stirring at 0° C. for 3 hours. After confirming that the reaction had been completed by GC analysis, the reaction mixture was poured into and mixed with a mixture of 1,500 mL of heptane and 1,500 mL of water at 0° C. The mixture was separated into an organic layer and an aqueous layer by standing still, so as to attain extraction to the organic layer. The resulting organic layer was fractionated and washed with water, followed by drying over anhydrous magnesium sulfate. The resulting organic layer was purified by silica gel column chromatography using heptane as eluent, and the solvent was removed by distillation under reduced pressure. The resulting residue was distilled under reduced pressure to obtain 103.3 g of 8-vinyl-1,4-dioxaspiro[4,5]decane (22) as a colorless transparent liquid. under cooling with ice by further stirring at 0° C. for 3 hours the reaction mixture was poured into and The mixture was separated into an organic layer extraction to the organic layer washed with water by drying over anhydrous magnesium sulfate The resulting organic layer was purified by silica gel column chromatography the solvent was removed by distillation under reduced pressure The resulting residue was distilled under reduced pressure