methyl 2-cyclohexylideneacetate

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

Procedure: 2.184 g trimethylphosphonoacetate was dissolved in DCM, stirred on ice-water bath, and 384 mg NaH was added. After 6 hours 980 mg cyclohexanone was added into the reaction flask, and stirred at ambient temperature overnight. The next day, the reaction mixture was washed with water twice, saturated aqueous NaCl solution once, dried over anhydrous MgSO4 for 2 hours, filtrated, and the filtrate was dried under vacuum to give 1.227 g of the title crude product. stirred at ambient temperature overnight The next day, the reaction mixture was washed with water twice saturated aqueous NaCl solution once, dried over anhydrous MgSO4 for 2 hours filtrated the filtrate was dried under vacuum

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

Procedure: 2.184 g trimethylphosphonoacetate was dissolved in DCM, stirred on ice-water bath, and 384 mg NaH was added. After 6 hours 980 mg cyclohexanone was added into the reaction flask, and stirred at ambient temperature overnight. The next day, the reaction mixture was washed with water twice, saturated aqueous NaCl solution once, dried over anhydrous MgSO4 for 2 hours, filtrated, and the filtrate was dried under vacuum to give 1.227 g of the title crude product. stirred at ambient temperature overnight The next day, the reaction mixture was washed with water twice saturated aqueous NaCl solution once, dried over anhydrous MgSO4 for 2 hours filtrated the filtrate was dried under vacuum

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Step B To a suspension of CuI (7.61 g, 40 mmol) in anhydrous ethyl ether (20 mL) at 0° C. was added an ethyl ether solution (1.6 M) of MeLi (50 mL, 80 mmol) The reaction mixture was stirred at 0° C. for 10 min. The solvent was evaporated under reduced pressure, then dichloromethane (20 mL) was added under nitrogen at 0° C. The mixture was stirred for 5 min. The solvent was evaporated again. To the residue was added dichlormethane (20 mL), and the temperature of the mixture was lowered to −78° C. To the mixture was added chlorotrimethylsilane (4.3 g, 40 mmol) and a dichloromethane solution (20 mL) of cyclohexylidene-acetic acid methyl ester (3.1 g, 20 mmol). The reaction mixture was allowed to slowly warmed to 0° C. and stirred for 1 h. Aqueous saturated NH4Cl solution was added to quench the reaction. The mixture was extracted with ethyl ether twice. The organic layers were combined, dried over MgSO4, concentrated. The residue was purified by chromatography (EtOAc:hexanes=1:5) to give (1-methyl-cyclohexyl)-acetic acid methyl ester as a colorless oil (3.3 g, 97%). The solvent was evaporated under reduced pressure dichloromethane (20 mL) was added under nitrogen at 0° C The mixture was stirred for 5 min The solvent was evaporated again To the residue was added dichlormethane (20 mL) was lowered to −78° C to slowly warmed to 0° C. stirred for 1 h to quench the reaction The mixture was extracted with ethyl ether twice dried over MgSO4 concentrated The residue was purified by chromatography (EtOAc:hexanes=1:5)

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

Procedure: 2.184 g trimethylphosphonoacetate was dissolved in DCM, stirred on ice-water bath, and 384 mg NaH was added. After 6 hours 980 mg cyclohexanone was added into the reaction flask, and stirred at ambient temperature overnight. The next day, the reaction mixture was washed with water twice, saturated aqueous NaCl solution once, dried over anhydrous MgSO4 for 2 hours, filtrated, and the filtrate was dried under vacuum to give 1.227 g of the title crude product. stirred at ambient temperature overnight The next day, the reaction mixture was washed with water twice saturated aqueous NaCl solution once, dried over anhydrous MgSO4 for 2 hours filtrated the filtrate was dried under vacuum