ethyl 2-cyclohexylacetate

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Lithium diisopropylamide (56 mL of 1.8M, 100 mmol) was added to a solution of ethyl cyclohexylacetate (16.0 g, 100 mmol) in 50 mL tetrahydrofuran at -40° C. and the solution stirred for 0.5 hour. After further cooling to -70° C., 4,4'-difluorobenzophenone (10.9 g, 50 mmol) was added and the solution stirred for 1 hour at -70° C. and then allowed to warm to -10° C. during the next 2 hrs. The reaction was quenched with 2N hydrochloric acid and extracted with diethyl ether. The extracts were dried with magnesium sulfate and concentrated in vacuo. The residue was crystallized from hexane to give 158 g of the title compound; m.p. =118°-119° C. the solution stirred for 1 hour at -70° C. to warm to -10° C. during the next 2 hrs The reaction was quenched with 2N hydrochloric acid extracted with diethyl ether The extracts were dried with magnesium sulfate concentrated in vacuo The residue was crystallized from hexane

反応条件: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Lithium diisopropylamide (56 mL of 1.8M, 100 mmol) was added to a solution of ethyl cyclohexylacetate (16.0 g, 100 mmol) in 50 mL tetrahydrofuran at -40° C. and the solution stirred for 0.5 hour. After further cooling to -70° C., 4,4'-difluorobenzophenone (10.9 g, 50 mmol) was added and the solution stirred for 1 hour at -70° C. and then allowed to warm to -10° C. during the next 2 hrs. The reaction was quenched with 2N hydrochloric acid and extracted with diethyl ether. The extracts were dried with magnesium sulfate and concentrated in vacuo. The residue was crystallized from hexane to give 158 g of the title compound; m.p. =118°-119° C. the solution stirred for 1 hour at -70° C. to warm to -10° C. during the next 2 hrs The reaction was quenched with 2N hydrochloric acid extracted with diethyl ether The extracts were dried with magnesium sulfate concentrated in vacuo The residue was crystallized from hexane

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Diisopropylamine (2.71 ml, 1.1 eq.) was added to dry THF (10 ml) and cooled to -78° C. N-Butyllithium (11.01 ml of 1.6 Molar solution, 1.0 eq.) was added and the mixture stirred at -78° C. for 0.5 hour. To this mixture was then added dropwise a solution of ethyl-2-cyclohexylacetate (3.0 g, 1.0 eq.) in THF (20 ml) at -78° C. and stirred for 0.5 hour. DMPU (2.13 ml, 1.0 eq.) in THF (20 ml) was added dropwise and allowed to stir at -78° C. for 10 minutes. To this mixture was added 1-bromo-2-chloroethane (1.46 ml, 1.0 eq.) in THF (10 ml) and the mixture stirred at -5° C. for 15 minutes. The mixture was then warmed to room temperature and stirred for 1.0 hour. The mixture was cooled to 0° C., quenched with saturated ammonium chloride solution, extracted with ethyl ether and the ether layer was washed three times with water. The organic layer was separated, dried over K2CO3 and the solvent removed to provide 3.6 g of product. This was fractionally distilled to provide 3.0 g of product Boiling Point 66°-70° C. at 0.05 mmHg. stirred for 0.5 hour to stir at -78° C. for 10 minutes the mixture stirred at -5° C. for 15 minutes The mixture was then warmed to room temperature stirred for 1.0 hour The mixture was cooled to 0° C. quenched with saturated ammonium chloride solution extracted with ethyl ether the ether layer was washed three times with water The organic layer was separated dried over K2CO3 the solvent removed

反応条件: temp:-70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Lithium diisopropylamide (56 mL of 1.8M, 100 mmol) was added to a solution of ethyl cyclohexylacetate (16.0 g, 100 mmol) in 50 mL tetrahydrofuran at -40° C. and the solution stirred for 0.5 hour. After further cooling to -70° C., 4,4'-difluorobenzophenone (10.9 g, 50 mmol) was added and the solution stirred for 1 hour at -70° C. and then allowed to warm to -10° C. during the next 2 hrs. The reaction was quenched with 2N hydrochloric acid and extracted with diethyl ether. The extracts were dried with magnesium sulfate and concentrated in vacuo. The residue was crystallized from hexane to give 158 g of the title compound; m.p. =118°-119° C. the solution stirred for 1 hour at -70° C. to warm to -10° C. during the next 2 hrs The reaction was quenched with 2N hydrochloric acid extracted with diethyl ether The extracts were dried with magnesium sulfate concentrated in vacuo The residue was crystallized from hexane