prop-2-enyl 2-oxocyclopentane-1-carboxylate

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

実験手順: A stirred solution of diallyl adipate (4.53 g, 20 mmol) in anhydrous tetrahydrofuran (100 mL) was cooled to 0° C. and treated with lithium bis(trimethylsilyl)amide (40 mL, 1.0 N in THF, 40 mmol). After the addition was complete, the solution was warmed to room temperature and stirred for 2 h. The solution was then recooled to 0° C. and treated with acetic acid (2.53 mL, 44 mmol) in a dropwise manner. The turbid mixture was warmed to room temperature and filtered. The filtrate was concentrated, dissolved in minimal dichloromethane and purified by flash column chromatography (silica gel, dichloromethane) to afford allyl 2-oxocyclopentanecarboxylate (2.62 g, 78%) as a colorless oil. Characterization data is same as that observed from method A. After the addition was then recooled to 0° C. The turbid mixture was warmed to room temperature filtered The filtrate was concentrated dissolved in minimal dichloromethane purified by flash column chromatography (silica gel, dichloromethane)

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

実験手順: A stirred solution of methyl 2-oxocyclopentanecarboxylate (4.26 g, 30 mmol) and allyl alcohol (10.2 mL, 150 mmol) in anhydrous toluene (25 mL) was treated with powdered zinc (0.40 g, 6 mmol), refluxed for 48 h, and cooled to room temperature. The suspension was filtered, the filter cake rinsed with toluene, and the filtrate concentrated to afford allyl 2-oxocyclopentanecarboxylate (5.01 g, 99%) as a colorless oil. 1H NMR (CDCl3, 300 MHz) δ 5.89 (ddt, J1=15.9 Hz, J2=10.5 Hz, J3=4.8 Hz, 1 H), 5.33 (dtd, J1=15.9 Hz, J2=2.7 Hz, J3=1.4 Hz, 1 H), 5.23 (dtd, J1=10.5 Hz, J2=2.7 Hz, J3=1.4 Hz, 1 H), 4.83-4.75 (m, 1 H), 3.18 (t, J=9.0 Hz, 1 H), 2.41-2.23 (m, 4 H), 2.22-2.07 (m, 1 H), 1.94-1.80 (m, 1 H); MS (+CI): m/z for C9H12O3: expected 168.1; found 169.1 (M+H)+. refluxed for 48 h The suspension was filtered the filter cake rinsed with toluene the filtrate concentrated

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

実験手順: A stirred solution of methyl 2-oxocyclopentanecarboxylate (4.26 g, 30 mmol) and allyl alcohol (10.2 mL, 150 mmol) in anhydrous toluene (25 mL) was treated with powdered zinc (0.40 g, 6 mmol), refluxed for 48 h, and cooled to room temperature. The suspension was filtered, the filter cake rinsed with toluene, and the filtrate concentrated to afford allyl 2-oxocyclopentanecarboxylate (5.01 g, 99%) as a colorless oil. 1H NMR (CDCl3, 300 MHz) δ 5.89 (ddt, J1=15.9 Hz, J2=10.5 Hz, J3=4.8 Hz, 1 H), 5.33 (dtd, J1=15.9 Hz, J2=2.7 Hz, J3=1.4 Hz, 1 H), 5.23 (dtd, J1=10.5 Hz, J2=2.7 Hz, J3=1.4 Hz, 1 H), 4.83-4.75 (m, 1 H), 3.18 (t, J=9.0 Hz, 1 H), 2.41-2.23 (m, 4 H), 2.22-2.07 (m, 1 H), 1.94-1.80 (m, 1 H); MS (+CI): m/z for C9H12O3: expected 168.1; found 169.1 (M+H)+. refluxed for 48 h The suspension was filtered the filter cake rinsed with toluene the filtrate concentrated

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

実験手順: To a stirring solution of diallyl adipate (4.53 g, 20 mmol) in anhydrous tetrahydrofuran (100 mL) at 0° C. was added lithium bis(trimethylsilyl)amide (40 mL, 1.0 N in THF, 40 mmol). After the addition was complete, the solution was warmed to room temperature and stirred for 2 hours. The reaction mixture was again cooled to 0° C. and the acidified by introducing acetic acid (2.53 mL, 44 mmol) in a dropwise manner. The addition of acetic acid resulted in a turbid mixture which mixture was warmed to room temperature and filtered. The filtrate obtained was concentrated, dissolved in minimal amount of dichloromethane and purified by flash column chromatography (silica gel, dichloromethane) to afford allyl 2-oxocyclopentanecarboxylate (2.62 g, 78%) as a colorless oil. The NMR spectrum for the purified product was the same as that observed for allyl 2-oxocyclopentanecarboxylate prepared using method A. After the addition The reaction mixture was again cooled to 0° C. resulted in a turbid mixture which mixture was warmed to room temperature filtered The filtrate obtained was concentrated dissolved in minimal amount of dichloromethane purified by flash column chromatography (silica gel, dichloromethane)

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

実験手順: To a stirred solution of methyl 2-oxocyclopentanecarboxylate (4.26 g, 30 mmol) and allyl alcohol (10.2 mL, 150 mmol) in anhydrous toluene (25 mL) was added powdered zinc (0.40 g, 6 mmol). After refluxing the mixture for 48 h, it was cooled to room temperature and the suspension was filtered. The filter cake was rinsed with toluene and the combined filtrate was concentrated to afford allyl 2-oxocyclopentanecarboxylate (5.01 g, 99%) as a colorless oil. 1H NMR (CDCl3, 300 MHz) δ 5.89 (ddt, J1=15.9 Hz, J2=10.5 Hz, J3=4.8 Hz, 1 H), 5.33 (dtd, J1=15.9 Hz, J2=2.7 Hz, J3=1.4 Hz, 1 H), 5.23 (dtd, J1=10.5 Hz, J2=2.7 Hz, J3=1.4 Hz, 1 H), 4.83-4.75 (m, 1 H), 3.18 (t, J=9.0 Hz, 1 H), 2.41-2.23 (m, 4 H), 2.22-2.07 (m, 1 H), 1.94-1.80 (m, 1 H); MS (+CI): m/z for C9H12O3: expected 168.1; found 169.1 (M+H)+. After refluxing the mixture for 48 h the suspension was filtered The filter cake was rinsed with toluene the combined filtrate was concentrated

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

実験手順: A stirred solution of diallyl adipate (4.53 g, 20 mmol) in anhydrous tetrahydrofuran (100 mL) was cooled to 0° C. and treated with lithium bis(trimethylsilyl)amide (40 mL, 1.0 N in THF, 40 mmol). After the addition was complete, the solution was warmed to room temperature and stirred for 2 h. The solution was then recooled to 0° C. and treated with acetic acid (2.53 mL, 44 mmol) in a dropwise manner. The turbid mixture was warmed to room temperature and filtered. The filtrate was concentrated, dissolved in minimal dichloromethane and purified by flash column chromatography (silica gel, dichloromethane) to afford allyl 2-oxocyclopentanecarboxylate (2.62 g, 78%) as a colorless oil. Characterization data is same as that observed from method A. After the addition was then recooled to 0° C. The turbid mixture was warmed to room temperature filtered The filtrate was concentrated dissolved in minimal dichloromethane purified by flash column chromatography (silica gel, dichloromethane)

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

実験手順: A stirred solution of methyl 2-oxocyclopentanecarboxylate (4.26 g, 30 mmol) and allyl alcohol (10.2 mL, 150 mmol) in anhydrous toluene (25 mL) was treated with powdered zinc (0.40 g, 6 mmol), refluxed for 48 h, and cooled to room temperature. The suspension was filtered, the filter cake rinsed with toluene, and the filtrate concentrated to afford allyl 2-oxocyclopentanecarboxylate (5.01 g, 99%) as a colorless oil. 1H NMR (CDCl3, 300 MHz) δ 5.89 (ddt, J1=15.9 Hz, J2=10.5 Hz, J3=4.8 Hz, 1 H), 5.33 (dtd, J1=15.9 Hz, J2=2.7 Hz, J3=1.4 Hz, 1 H), 5.23 (dtd, J1=10.5 Hz, J2=2.7 Hz, J3=1.4 Hz, 1 H), 4.83-4.75 (m, 1 H), 3.18 (t, J=9.0 Hz, 1 H), 2.41-2.23 (m, 4 H), 2.22-2.07 (m, 1 H), 1.94-1.80 (m, 1 H); MS (+CI): m/z for C9H12O3: expected 168.1; found 169.1 (M+H)+. refluxed for 48 h The suspension was filtered the filter cake rinsed with toluene the filtrate concentrated