ethyl cyclohex-3-ene-1-carboxylate

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

Conditions: temp:85.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of 1.25 g (2.60 mM) of 50% sodium hydride in 10 ml of toluene is added dropwise a solution of 2.01 g (1.30 mM) of ethyl 3-cyclohexenylcarboxylate 11 and 0.96 g (2.34 mM) of acetonitrile in 4 ml of toluene under nitrogen atmosphere in an hour and the mixture is stirred at 85° C. for 8 hours. After cooling, ice-cold water is added to the mixture. The aqueous phase is separated, washed with toluene, made acid with 10% hydrochloric acid and extracted with toluene. The extracted solution is washed with a dilute aqueous sodium hydrogencarbonate, and then with water, dried on magnesium sulfate and evaporated under reduced pressure. The resulting residue is chromatographed over silica gel and eluted with chloroform to give 1.91 g of the titled compound 8 as an yellow oil in 98.4% yield, After cooling ice-cold water is added to the mixture The aqueous phase is separated washed with toluene extracted with toluene The extracted solution is washed with a dilute aqueous sodium hydrogencarbonate with water, dried on magnesium sulfate evaporated under reduced pressure The resulting residue is chromatographed over silica gel eluted with chloroform

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

Procedure: To a solution of ethyl cyclohex-3-ene-1-carboxylate (14.0 g, 90 mmol) in CH2Cl2 (350 mL) was added meta-chloroperbenzoic acid (18.9 g, 110 mmol) at 0° C. The reaction mixture was stirred at room temperature for 2.5 hours. After cooling to 0° C., the reaction was neutralized with aqueous Na2CO3 solution. The organic layer was collected and washed with water and brine, then was dried over MgSO4 and concentrated in vacuo to a light oil (17.8 g), which was used in the next reaction with further purification. After cooling to 0° C. The organic layer was collected washed with water and brine was dried over MgSO4 concentrated in vacuo to a light oil (17.8 g), which was used in the next reaction with further purification

Conditions: temp:85.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of 1.25 g (2.60 mM) of 50% sodium hydride in 10 ml of toluene is added dropwise a solution of 2.01 g (1.30 mM) of ethyl 3-cyclohexenylcarboxylate 11 and 0.96 g (2.34 mM) of acetonitrile in 4 ml of toluene under nitrogen atmosphere in an hour and the mixture is stirred at 85° C. for 8 hours. After cooling, ice-cold water is added to the mixture. The aqueous phase is separated, washed with toluene, made acid with 10% hydrochloric acid and extracted with toluene. The extracted solution is washed with a dilute aqueous sodium hydrogencarbonate, and then with water, dried on magnesium sulfate and evaporated under reduced pressure. The resulting residue is chromatographed over silica gel and eluted with chloroform to give 1.91 g of the titled compound 8 as an yellow oil in 98.4% yield, After cooling ice-cold water is added to the mixture The aqueous phase is separated washed with toluene extracted with toluene The extracted solution is washed with a dilute aqueous sodium hydrogencarbonate with water, dried on magnesium sulfate evaporated under reduced pressure The resulting residue is chromatographed over silica gel eluted with chloroform