benzyl cyclohex-3-ene-1-carboxylate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: (±)-3-Cyclohexene-1-carboxylic acid (50 g) was dissolved in N,N-dimethylformamide (550 ml), and triethylamine (170 ml) and benzyl bromide (61 ml) were added under ice cooling to stir the mixture at room temperature for 12 hours. Water was added, extraction was conducted with ethyl acetate, and the resultant organic layer was washed with saturated aqueous solution of sodium chloride and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:1) to obtain the title compound (70.8 g). extraction the resultant organic layer was washed with saturated aqueous solution of sodium chloride dried over anhydrous magnesium sulfate The solvent was distilled off under reduced pressure the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:1)

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

Procedure: Benzyl (±)-3-cyclohexene-1-carboxylate (40 g) was dissolved in dichloromethane (500 ml), and m-chloroperbenzoic acid (86 g) was added under ice cooling to stir the mixture for 2 hours. After a 10% aqueous solution of sodium thiosulfate was added to conduct stirring for 20 minutes, an organic layer was separated, washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated saline and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:9) to obtain the title compound (23.4 g) and benzyl (1R,3R*,4S*)-3,4-epoxycyclohexane-1-carboxylate (12.1 g) as colorless oils. to conduct stirring for 20 minutes an organic layer was separated washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated saline dried over anhydrous magnesium sulfate The solvent was distilled off under reduced pressure the residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:9)

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

Procedure: Benzyl (±)-3-cyclohexene-1-carboxylate (40 g) was dissolved in dichloromethane (500 ml), and m-chloroperbenzoic acid (86 g) was added under ice cooling to stir the mixture for 2 hours. After a 10% aqueous solution of sodium thiosulfate was added to conduct stirring for 20 minutes, an organic layer was separated, washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated saline and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:9) to obtain the title compound (23.4 g) and benzyl (1R,3R*,4S*)-3,4-epoxycyclohexane-1-carboxylate (12.1 g) as colorless oils. to conduct stirring for 20 minutes an organic layer was separated washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated saline dried over anhydrous magnesium sulfate The solvent was distilled off under reduced pressure the residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:9)

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

Procedure: (±)-3-Cyclohexene-1-carboxylic acid (50 g) was dissolved in N,N-dimethylformamide (550 ml), and triethylamine (170 ml) and benzyl bromide (61 ml) were added under ice cooling to stir the mixture at room temperature for 12 hours. Water was added, extraction was conducted with ethyl acetate, and the resultant organic layer was washed with saturated saline and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:1) to obtain the title compound (70.8 g) as a reddish brown oil. extraction the resultant organic layer was washed with saturated saline dried over anhydrous magnesium sulfate The solvent was distilled off under reduced pressure the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:1)

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

Procedure: Benzyl (±)-3-cyclohexene-1-carboxylate (40 g) was dissolved in dichloromethane (500 ml), and m-chloroperbenzoic acid (86 g) was added under ice cooling to stir the mixture for 2 hours. After a 10% aqueous solution of sodium thiosulfate was added to conduct stirring for 20 minutes, an organic layer was separated, washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated saline and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:9) to obtain the title compound (23.4 g) and benzyl (1R*,3R*,4S*)-3,4-epoxycyclohexane-1-carboxylate (12.1 g) as colorless oils. to conduct stirring for 20 minutes an organic layer was separated washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated saline dried over anhydrous magnesium sulfate The solvent was distilled off under reduced pressure the residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:9)

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

Procedure: Benzyl (±)-3-cyclohexene-1-carboxylate (40 g) was dissolved in dichloromethane (500 ml), and m-chloroperbenzoic acid (86 g) was added under ice cooling to stir the mixture for 2 hours. After a 10% aqueous solution of sodium thiosulfate was added to conduct stirring for 20 minutes, an organic layer was separated, washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated saline and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:9) to obtain the title compound (23.4 g) and benzyl (1R*,3R*,4S*)-3,4-epoxycyclohexane-1-carboxylate (12.1 g) as colorless oils. to conduct stirring for 20 minutes an organic layer was separated washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated saline dried over anhydrous magnesium sulfate The solvent was distilled off under reduced pressure the residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:9)

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

Procedure: (±)-3-Cyclohexene-1-carboxylic acid (50 g) was dissolved in N,N-dimethylformamide (550 ml), and triethylamine (170 ml) and benzyl bromide (61 ml) were added under ice cooling to stir the mixture at room temperature for 12 hours. Water was added, extraction was conducted with ethyl acetate, and the resultant organic layer was washed with saturated saline and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:1) to obtain the title compound (70.8 g) as a reddish brown oil. extraction the resultant organic layer was washed with saturated saline dried over anhydrous magnesium sulfate The solvent was distilled off under reduced pressure the residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:1)

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: (±)-3-Cyclohexene-1-carboxylic acid (50 g) was dissolved in N,N-dimethylformamide (550 mL), and to the solution were added triethylamine (170 mL) and benzyl bromide (61 mL) under ice cooling, followed by stirring at room temperature for 12 hours. Water was added to the resultant mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and was dried over anhydrous magnesium sulfate. The solvent was distilled away under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1), to thereby give the title compound (70.8 g). the mixture was extracted with ethyl acetate The organic layer was washed with saturated brine was dried over anhydrous magnesium sulfate The solvent was distilled away under reduced pressure the residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1)