3-oxooctanoic acid

反応条件: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 8.7g (0.05 m) of hexanoylacetic acid and 12.7 g (0.10m) of oxalyl chloride were mixed together at room temperature. The reaction was heated gradually over one hour to 50-60° C., then to 60-70° C. under aspirator pressure for one hour. The reaction mixture was diluted with 125 ml hexane, washed with 3×100 ml ice water, dried over 20 g MgSO4, and roto-vapped at 50° C. to yield an oil (9.4 g, 98% yield). washed with 3×100 ml ice water dried over 20 g MgSO4

反応条件: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 8.7g (0.05 m) of hexanoylacetic acid and 12.7 g (0.10m) of oxalyl chloride were mixed together at room temperature. The reaction was heated gradually over one hour to 50-60° C., then to 60-70° C. under aspirator pressure for one hour. The reaction mixture was diluted with 125 ml hexane, washed with 3×100 ml ice water, dried over 20 g MgSO4, and roto-vapped at 50° C. to yield an oil (9.4 g, 98% yield). washed with 3×100 ml ice water dried over 20 g MgSO4

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

実験手順: 8.7 g (0.05 m) of hexanoylacetic acid and 12.7 g (0.10 m) of oxalyl chloride were mixed together at room temperature. The reaction was heated gradually over one hour to 50°-60° C., then to 60°-70° C. under aspirator pressure for one hour. The reaction mixture was diluted with 125 ml hexane, washed with 3×100 ml ice water, dried over 20 g MgSO4, and roto-vapped at 50° C. to yield an oil (9.4 g, 98% yield). The reaction was heated gradually over one hour to 50°-60° C. washed with 3×100 ml ice water dried over 20 g MgSO4

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

実験手順: 8.7 g (0.05 m) of hexanoylacetic acid and 12.7 g (0.10 m) of oxalyl chloride were mixed together at room temperature. The reaction was heated gradually over one hour to 50°-60° C., then to 60°-70° C. under aspirator pressure for one hour. The reaction mixture was diluted with 125 ml hexane, washed with 3×100 ml ice water, dried over 20 g MgSO4, and roto-vapped at 50° C. to yield an oil (9.4 g, 98% yield). The reaction was heated gradually over one hour to 50°-60° C. washed with 3×100 ml ice water dried over 20 g MgSO4

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

実験手順: A stirred solution of bis-trimethylsilyl malonate (21.6 g, 71.5 mmol) in 100 mL of anhydrous diethyl ether was cooled to −78° C. To this solution, n-butyl lithium (1.6 M in ether, 44.7 mL, 71.5 mmol) was added slowly, keeping the temperature below −60° C. Upon completion of addition, the reaction was allowed to warm to −10° C., at which time hexanoyl chloride (5 mL, 35.75 mmol) was added quickly and allowed to stir for 30 minutes. Next, 150 mL of a cold, aq. 5% sodium bicarbonate solution was added, and the resulting solution was stirred vigorously for 30 minutes. The aq. layer was separated out and acidified with cold 4N sulfuric acid until pH=2. The aq. layer was then extracted 2×50 mL with diethyl ether, dried over MgSO4, and concentrated down in vacuo to afford a white solid. This solid could be further purified by recrystallization from hexane, if necessary. 4.9 g, 87% yield. 1H NMR (300 MHz, CDCl3) δ=3.49 (s, 2H, CH2), 2.59 (t, 2H, J=7.3 Hz, CH2), 1.64 (p, 2H, J=7.4 Hz, CH2), 1.34 (m, 4H, CH2CH2), 0.92 (t, 3H, J=6.9 Hz, CH3); 13C NMR (75 MHz, CDCl3) δ=204.4, 182.8, 87.9, 48.1, 43.4, 31.3, 23.5, 14.1 ppm. the temperature below −60° C Upon completion of addition was added quickly the resulting solution was stirred vigorously for 30 minutes The aq. layer was separated out The aq. layer was then extracted 2×50 mL with diethyl ether dried over MgSO4 concentrated down in vacuo to afford a white solid This solid could be further purified by recrystallization from hexane

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

実験手順: A stirred solution of bis-trimethylsilyl malonate (21.6 g, 71.5 mmol) in 100 mL of anhydrous diethyl ether was cooled to −78° C. To this solution, n-butyl lithium (1.6 M in ether, 44.7 mL, 71.5 mmol) was added slowly, keeping the temperature below −60° C. Upon completion of addition, the reaction was allowed to warm to −10° C., at which time hexanoyl chloride (5 mL, 35.75 mmol) was added quickly and allowed to stir for 30 minutes. Next, 150 mL of a cold, aq. 5% sodium bicarbonate solution was added, and the resulting solution was stirred vigorously for 30 minutes. The aq. layer was separated out and acidified with cold 4N sulfuric acid until pH=2. The aq. layer was then extracted 2×50 mL with diethyl ether, dried over MgSO4, and concentrated down in vacuo to afford a white solid. This solid could be further purified by recrystallization from hexane, if necessary. 4.9 g, 87% yield. 1H NMR (300 MHz, CDCl3) δ=3.49 (s, 2H, CH2), 2.59 (t, 2H, J=7.3 Hz, CH2), 1.64 (p, 2H, J=7.4 Hz, CH2), 1.34 (m, 4H, CH2CH2), 0.92 (t, 3H, J=6.9 Hz, CH3); 13C NMR (75 MHz, CDCl3) δ=204.4, 182.8, 87.9, 48.1, 43.4, 31.3, 23.5, 14.1 ppm. the temperature below −60° C Upon completion of addition was added quickly the resulting solution was stirred vigorously for 30 minutes The aq. layer was separated out The aq. layer was then extracted 2×50 mL with diethyl ether dried over MgSO4 concentrated down in vacuo to afford a white solid This solid could be further purified by recrystallization from hexane

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

実験手順: A stirred solution of bis-trimethylsilyl malonate (21.6 g, 71.5 mmol) in 100 mL of anhydrous diethyl ether was cooled to −78° C. To this solution, n-butyl lithium (1.6 M in ether, 44.7 mL, 71.5 mmol) was added slowly, keeping the temperature below −60° C. Upon completion of addition, the reaction was allowed to warm to −10° C., at which time hexanoyl chloride (5 mL, 35.75 mmol) was added quickly and allowed to stir for 30 minutes. Next, 150 mL of a cold, aq. 5% sodium bicarbonate solution was added, and the resulting solution was stirred vigorously for 30 minutes. The aq. layer was separated out and acidified with cold 4N sulfuric acid until pH=2. The aq. layer was then extracted 2×50 mL with diethyl ether, dried over MgSO4, and concentrated down in vacuo to afford a white solid. This solid could be further purified by recrystallization from hexane, if necessary. 4.9 g, 87% yield. 1H NMR (300 MHz, CDCl3) δ=3.49 (s, 2H, CH2), 2.59 (t, 2H, J=7.3 Hz, CH2), 1.64 (p, 2H, J=7.4 Hz, CH2), 1.34 (m, 4H, CH2CH2), 0.92 (t, 3H, J=6.9 Hz, CH3); 13C NMR (75 MHz, CDCl3) δ=204.4, 182.8, 87.9, 48.1, 43.4, 31.3, 23.5, 14.1 ppm. the temperature below −60° C Upon completion of addition was added quickly the resulting solution was stirred vigorously for 30 minutes The aq. layer was separated out The aq. layer was then extracted 2×50 mL with diethyl ether dried over MgSO4 concentrated down in vacuo to afford a white solid This solid could be further purified by recrystallization from hexane

反応条件: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 8.7 gm (0.05 mole) of hexanoylacetic acid and 12.7 gm (0.10 mole) of oxalyl chloride were mixed together at room temperature. The reaction was heated gradually over one hour at 50-60° C. for about two hours. Excess oxalyl chloride was removed under reduced pressure to yield an oil that exhibits no --OH stretch by IR. Weight was 9.6 gm. Excess oxalyl chloride was removed under reduced pressure to yield an oil that

反応条件: temp:55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 8.7g (0.05 m) of hexanoylacetic acid and 12.7 g (0.10m) of oxalyl chloride were mixed together at room temperature. The reaction was heated gradually over one hour to 50-60° C., then to 60-70° C. under aspirator pressure for one hour. The reaction mixture was diluted with 125 ml hexane, washed with 3×100 ml ice water, dried over 20 g MgSO4, and roto-vapped at 50° C. to yield an oil (9.4 g, 98% yield). washed with 3×100 ml ice water dried over 20 g MgSO4

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

実験手順: 8.7 g (0.05 m) of hexanoylacetic acid and 12.7 g (0.10 m) of oxalyl chloride were mixed together at room temperature. The reaction was heated gradually over one hour to 50°-60° C., then to 60°-70° C. under aspirator pressure for one hour. The reaction mixture was diluted with 125 ml hexane, washed with 3×100 ml ice water, dried over 20 g MgSO4, and roto-vapped at 50° C. to yield an oil (9.4 g, 98% yield). The reaction was heated gradually over one hour to 50°-60° C. washed with 3×100 ml ice water dried over 20 g MgSO4