ethyl 2-methyl-4-oxocyclohexane-1-carboxylate

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

Procedure: To a cooled (0° C.) suspension of (methoxymethyl)triphenylphosphonium chloride (155 g, 452 mmol) in THF (700 mL) was added potassium tert-butoxide (1.0 M in THF, 452 mL, 452 mmol) at such a rate that the internal temperature did not exceed 7° C. The mixture was stirred for 1 hour at 0° C., and then a solution of ethyl 2-methyl-4-oxocyclohexanecarboxylate (64 g, 347 mmol) in THF (150 mL) was added via canula at such a rate that the internal temperature did not exceed 7° C. The mixture was then slowly warmed to room temperature and stirred for 14 hours. The reaction mixture was then cooled to 10° C. and diluted with water (200 mL) followed by 6 M HCl (500 mL). The resulting mixture was stirred for 3 hours, and then diluted with additional water (400 mL) and EtOAc (700 mL). The organic layer was separated, and the aqueous layer was extracted a second time with EtOAc (700 mL). The organic layers were combined, dried over MgSO4, filtered, absorbed on silica gel, and purified by silica gel chromatography to afford ethyl 4-formyl-2-methylcyclohexanecarboxylate, which was used immediately in the subsequent step. To a cooled did not exceed 7° C did not exceed 7° C The mixture was then slowly warmed to room temperature stirred for 14 hours The reaction mixture was then cooled to 10° C. The resulting mixture was stirred for 3 hours The organic layer was separated the aqueous layer was extracted a second time with EtOAc (700 mL) dried over MgSO4 filtered absorbed on silica gel purified by silica gel chromatography

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

Procedure: To a cooled (0° C.) suspension of (methoxymethyl)triphenylphosphonium chloride (155 g, 452 mmol) in THF (700 mL) was added potassium tert-butoxide (1.0 M in THF, 452 mL, 452 mmol) at such a rate that the internal temperature did not exceed 7° C. The mixture was stirred for 1 hour at 0° C., and then a solution of ethyl 2-methyl-4-oxocyclohexanecarboxylate (64 g, 347 mmol) in THF (150 mL) was added via canula at such a rate that the internal temperature did not exceed 7° C. The mixture was then slowly warmed to room temperature and stirred for 14 hours. The reaction mixture was then cooled to 10° C. and diluted with water (200 mL) followed by 6 M HCl (500 mL). The resulting mixture was stirred for 3 hours, and then diluted with additional water (400 mL) and EtOAc (700 mL). The organic layer was separated, and the aqueous layer was extracted a second time with EtOAc (700 mL). The organic layers were combined, dried over MgSO4, filtered, absorbed on silica gel, and purified by silica gel chromatography to afford ethyl 4-formyl-2-methylcyclohexanecarboxylate, which was used immediately in the subsequent step. To a cooled did not exceed 7° C did not exceed 7° C The mixture was then slowly warmed to room temperature stirred for 14 hours The reaction mixture was then cooled to 10° C. The resulting mixture was stirred for 3 hours The organic layer was separated the aqueous layer was extracted a second time with EtOAc (700 mL) dried over MgSO4 filtered absorbed on silica gel purified by silica gel chromatography