3-methylcyclopent-2-en-1-one

反応条件: temp:0.00; pressure:0.00; stir:

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

実験手順: To a solution obtained by adding 350 ml of dehydrated diethyl ether to 450 ml (0.90 mol) of a tert-butylmagnesium chloride/diethyl ether solution (concentration: 2.0 mol/liter), a solution of 43.7 g (0.45 mmol) of 3-methylcyclopentenone in 150 ml of dehydrated diethyl ether was dropwise added in a nitrogen atmosphere at 0° C. with ice cooling, followed by stirring at room temperature for 15 hours. To the reaction solution, a solution of 80.0 g (1.50 mol) of ammonium chloride in 350 ml of water was dropwise added at 0° C. with ice cooling. To the resulting solution, 2500 ml of water was added, followed by stirring. Then, the organic phase was separated and washed with water. To the organic phase, 82 ml of a 10% hydrochloric acid aqueous solution was added at 0° C. with ice cooling, followed by stirring at room temperature for 6 hours. The organic phase was separated from the reaction solution, washed with water, a saturated sodium hydrogencarbonate aqueous solution, water and a saturated saline solution, and then dried over anhydrous magnesium sulfate. The drying agent was filtered, and from the filtrate the solvent was distilled off to obtain a liquid. The liquid was subjected to vacuum distillation (45-47° C./10 mmHg) to obtain 14.6 g of a light yellow liquid. The analyzed values are given below. To a solution obtained by stirring Then, the organic phase was separated washed with water To the organic phase, 82 ml of a 10% hydrochloric acid aqueous solution was added at 0° C. with ice cooling by stirring at room temperature for 6 hours The organic phase was separated from the reaction solution washed with water a saturated sodium hydrogencarbonate aqueous solution, water and a saturated saline solution, and then dried over anhydrous magnesium sulfate The drying agent was filtered from the filtrate the solvent was distilled off to obtain a liquid The liquid was subjected to vacuum distillation (45-47° C./10 mmHg)

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

実験手順: To a solution obtained by adding 350 ml of dehydrated diethyl ether to 450 ml (0.90 mol) of a tert-butylmagnesium chloride/diethyl ether solution (concentration: 2.0 mol/liter), a solution of 43.7 g (0.45 mmol) of 3-methylcyclopentenone in 150 ml of dehydrated diethyl ether was dropwise added in a nitrogen atmosphere at 0° C. with ice cooling, followed by stirring at room temperature for 15 hours. To the reaction solution, a solution of 80.0 g (1.50 mol) of ammonium chloride in 350 ml of water was dropwise added at 0° C. with ice cooling. To the resulting solution, 2500 ml of water was added, followed by stirring. Then, the organic phase was separated and washed with water. To the organic phase, 82 ml of a 10% hydrochloric acid aqueous solution was added at 0° C. with ice cooling, followed by stirring at room temperature for 6 hours. The organic phase was separated from the reaction solution, washed with water, a saturated sodium hydrogencarbonate aqueous solution, water and a saturated saline solution, and then dried over anhydrous magnesium sulfate. The drying agent was filtered, and from the filtrate the solvent was distilled off to obtain a liquid. The liquid was subjected to vacuum distillation (45-47° C./10 mmHg) to obtain 14.6 g of a light yellow liquid. The analyzed values are given below. To a solution obtained by stirring Then, the organic phase was separated washed with water To the organic phase, 82 ml of a 10% hydrochloric acid aqueous solution was added at 0° C. with ice cooling by stirring at room temperature for 6 hours The organic phase was separated from the reaction solution washed with water a saturated sodium hydrogencarbonate aqueous solution, water and a saturated saline solution, and then dried over anhydrous magnesium sulfate The drying agent was filtered from the filtrate the solvent was distilled off to obtain a liquid The liquid was subjected to vacuum distillation (45-47° C./10 mmHg)

反応条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 3-methyl-2-cyclopentenone 24.5 g (0.25 mole) and prenyl chloride 54 g (0.51 mole) was fed into a reaction flask containing 30 ml of toluene, sodium hydroxide 21.3 g, water 21.3 g and Aliquat 3361 g maintaining 100° C. The reaction mass was aged for 4 hours, cooled to 25° C. and neutralized with acetic acid. The organic layer was removed and distilled to give 20.5 g of 3-methyl-2-(3-methyl-2-butenyl)-2-cyclopenten-1-one. The 3-methyl-2-(3-methyl-2-butenyl)-2-cyclopenten-1-one had a Bp of 115° C. at 5 mmHg. was fed into a reaction flask The organic layer was removed distilled

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

実験手順: 3-Methylcyclopent-2-enone (1, 35.0 g, 0.36 mol) was reacted with ethylmagnesium chloride (2M in THF, 218 ml, 0.44 mol) in the presence of 1 mol % CuCl2 in THF (200 ml) as described in Example 1a. The crude product was distilled over a 15 cm Vigreux column (B.p. 50° C. at 5 Torr) to give 2b (32.0 g, 69% yield) as a colorless liquid. The crude product was distilled over a 15 cm Vigreux column (B.p. 50° C. at 5 Torr)

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

実験手順: 3-Methylcyclopent-2-enone (1, 35.0 g, 0.36 mol) was reacted with ethylmagnesium chloride (2M in THF, 218 ml, 0.44 mol) in the presence of 1 mol % CuCl2 in THF (200 ml) as described in Example 1a. The crude product was distilled over a 15 cm Vigreux column (B.p. 50° C. at 5 Torr) to give 2b (32.0 g, 69% yield) as a colorless liquid. The crude product was distilled over a 15 cm Vigreux column (B.p. 50° C. at 5 Torr)

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

実験手順: To a solution obtained by adding 350 ml of dehydrated diethyl ether to 450 ml (0.90 mol) of a tert-butylmagnesium chloride/diethyl ether solution (concentration: 2.0 mol/liter), a solution of 43.7 g (0.45 mmol) of 3-methylcyclopentenone in 150 ml of dehydrated diethyl ether was dropwise added in a nitrogen atmosphere at 0° C. with ice cooling, followed by stirring at room temperature for 15 hours. To the reaction solution, a solution of 80.0 g (1.50 mol) of ammonium chloride in 350 ml of water was dropwise added at 0° C. with ice cooling. To the resulting solution, 2500 ml of water was added, followed by stirring. Then, the organic phase was separated and washed with water. To the organic phase, 82 ml of a 10% hydrochloric acid aqueous solution was added at 0° C. with ice cooling, followed by stirring at room temperature for 6 hours. The organic phase was separated from the reaction solution, washed with water, a saturated sodium hydrogencarbonate aqueous solution, water and a saturated saline solution, and then dried over anhydrous magnesium sulfate. The drying agent was filtered, and from the filtrate the solvent was distilled off to obtain a liquid. The liquid was subjected to vacuum distillation (45-47° C./10 mmHg) to obtain 14.6 g of a light yellow liquid. The analyzed values are given below. To a solution obtained by stirring Then, the organic phase was separated washed with water To the organic phase, 82 ml of a 10% hydrochloric acid aqueous solution was added at 0° C. with ice cooling by stirring at room temperature for 6 hours The organic phase was separated from the reaction solution washed with water a saturated sodium hydrogencarbonate aqueous solution, water and a saturated saline solution, and then dried over anhydrous magnesium sulfate The drying agent was filtered from the filtrate the solvent was distilled off to obtain a liquid The liquid was subjected to vacuum distillation (45-47° C./10 mmHg)

反応条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 3-methyl-2-cyclopentenone 24.5 g (0.25 mole) and prenyl chloride 54 g (0.51 mole) was fed into a reaction flask containing 30 ml of toluene, sodium hydroxide 21.3 g, water 21.3 g and Aliquat 336 lg maintaining 100° C. The reaction mass was aged for 4 hours, cooled to 25° C. and neutralized with acetic acid. The organic layer was removed and distilled to give 20.5 g of 3-methyl-2-(3-methyl-2-butenyl)-2-cyclopenten-1-one. was fed into a reaction flask The organic layer was removed distilled

反応条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 3-methyl-2-cyclopentenone 24.5 g (0.25 mole) and prenyl chloride 54 g (0.51 mole) was fed into a reaction flask containing 30 ml of toluene, sodium hydroxide 21.3 g, water 21.3 g and Aliquat 336 lg maintaining 100° C. The reaction mass was aged for 4 hours, cooled to 25° C. and neutralized with acetic acid. The organic layer was removed and distilled to give 20.5 g of 3-methyl-2-(3-methyl-2-butenyl)-2-cyclopenten-1-one. was fed into a reaction flask The organic layer was removed distilled

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

実験手順: To a solution obtained by adding 350 ml of dehydrated diethyl ether to 450 ml (0.90 mol) of a tert-butylmagnesium chloride/diethyl ether solution (concentration: 2.0 mol/liter), a solution of 43.7 g (0.45 mmol) of 3-methylcyclopentenone in 150 ml of dehydrated diethyl ether was dropwise added in a nitrogen atmosphere at 0° C. with ice cooling, followed by stirring at room temperature for 15 hours. To the reaction solution, a solution of 80.0 g (1.50 mol) of ammonium chloride in 350 ml of water was dropwise added at 0° C. with ice cooling. To the resulting solution, 2500 ml of water was added, followed by stirring. Then, the organic phase was separated and washed with water. To the organic phase, 82 ml of a 10% hydrochloric acid aqueous solution was added at 0° C. with ice cooling, followed by stirring at room temperature for 6 hours. The organic phase was separated from the reaction solution, washed with water, a saturated sodium hydrogencarbonate aqueous solution, water and a saturated saline solution, and then dried over anhydrous magnesium sulfate. The drying agent was filtered, and from the filtrate the solvent was distilled off to obtain a liquid. The liquid was subjected to vacuum distillation (45-47° C./10 mmHg) to obtain 14.6 g of a light yellow liquid. The analyzed values are given below. To a solution obtained by stirring Then, the organic phase was separated washed with water To the organic phase, 82 ml of a 10% hydrochloric acid aqueous solution was added at 0° C. with ice cooling by stirring at room temperature for 6 hours The organic phase was separated from the reaction solution washed with water a saturated sodium hydrogencarbonate aqueous solution, water and a saturated saline solution, and then dried over anhydrous magnesium sulfate The drying agent was filtered from the filtrate the solvent was distilled off to obtain a liquid The liquid was subjected to vacuum distillation (45-47° C./10 mmHg)

反応条件: temp:0.00; pressure:0.00; stir:

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

実験手順: A solution of 25 g (0.26 mol) of 3-methyl-2cyclopenten-1-one in 100 mL of ether was added at −78° C. under argon atmosphere to a solution of phenyl litium in 200 mL of ether, previous prepared from 5.76 g (0.83 mol) of lithium and 44 mL (0.42 mol) of bromobenzene. The reaction mixture was stirred for 4 h and then treated with a 10% aq. solution of NH4Cl. The organic phase was collected, washed with water, dried with MgSO4 and concentrated. The residue was distilled at 54° C./1 mmHg. Yield 24.37 g (60%). The organic phase was collected washed with water dried with MgSO4 concentrated The residue was distilled at 54° C./1 mmHg