2,2,3,3-tetramethylcyclopropane-1-carbonitrile

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

Procedure: Obtained by operating as in example 87a, from 19.7 g (195 mmoles) of diisopropylamine, 122 ml (195 mmoles) of a 1.6M solution of n-butyllithium in hexane, 45 ml of 1,3-dimethylimidazolidin-2-one, 21.8 g of 2,2,3,3-tetramethylcyclopropanecarbonitrile (prepared according to patent FR 2,479,192), 51.9 g (180.5 mmoles) of the compound prepared in example 26a in 295 ml tetrahydrofuran. After distillation, there is obtained 20 g (yield=44.0%) of a thick yellow oil. b.p.0.8 =185°-205° C. Obtained After distillation

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

Procedure: Obtained by operating as in example 87a, from 19.7 g (195 mmoles) of diisopropylamine, 122 ml (195 mmoles) of a 1.6M solution of n-butyllithium in hexane, 45 ml of 1,3-dimethylimidazolidin-2-one, 21.8 g of 2,2,3,3-tetramethylcyclopropanecarbonitrile (prepared according to patent FR 2,479,192), 51.9 g (180.5 mmoles) of the compound prepared in example 26a in 295 ml tetrahydrofuran. After distillation, there is obtained 20 g (yield=44.0%) of a thick yellow oil. b.p.0.8 =185°-205° C. Obtained After distillation

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

Procedure: 9.15 ml of a cyclohexane solution of 1.75M of butyllithium were added with stirring under an inert atmosphere at -30° to -40° C. to a mixture of 2.49 ml of diisopropylamine and 5 ml of tetrahydrofuran and after 10 minutes of contact, the mixture was cooled to -60° to -70° C. A mixture of 4.068 g of 4-tolyl sulfonyl-4,3,3,-trimethyl-pentanenitrile in 15 ml of tetrahydrofuran were added to the mixture over 5 minutes and the mixture was stirred at -60° to -70° C. for 10 minutes after which the temperature was allowed to rise to 20° to 25° C. The mixture was stirred for one hour and was then poured into an iced aqueous saturated monosodium phosphate solution. The mixture was extracted with n-pentane and the organic phase was dried and evaporated to dryness under reduced pressure. The residue was distilled under reduced pressure to obtain 1.064 g of pure 2,2,3,3-tetramethyl-cyclopropane-carbonitrile with a boiling point of 58°-60° C. at 12-14 mm Hg and a melting point of 17° C. the mixture was cooled to -60° to -70° C were added to the mixture over 5 minutes to rise to 20° to 25° C The mixture was stirred for one hour The mixture was extracted with n-pentane the organic phase was dried evaporated to dryness under reduced pressure The residue was distilled under reduced pressure

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

Procedure: 9.15 ml of a cyclohexane solution of 1.75M of butyllithium were added with stirring under an inert atmosphere at -30° to -40° C. to a mixture of 2.49 ml of diisopropylamine and 5 ml of tetrahydrofuran and after 10 minutes of contact, the mixture was cooled to -60° to -70° C. A mixture of 4.068 g of 4-tolyl sulfonyl-4,3,3-trimethyl-pentanenitrile in 15 ml of tetrahydrofuran were added to the mixture over 5 minutes and the mixture was stirred at -60° to -70° C. for 10 minutes after which the temperature was allowed to rise to 20° to 25° C. The mixture was stirred for one hour and was then poured into an iced aqueous saturated monosodium phosphate solution. The mixture was extracted with n-pentane and the organic phase was dried and evaporated to dryness under reduced pressure. The residue was distilled under reduced pressure to obtain 1.064 g of pure 2,2,3,3-tetramethyl-cyclopropane-carbonitrile with a boiling point of 58°-60° C. at 12-14 mm Hg and a melting point of 17° C. the mixture was cooled to -60° to -70° C were added to the mixture over 5 minutes to rise to 20° to 25° C The mixture was stirred for one hour The mixture was extracted with n-pentane the organic phase was dried evaporated to dryness under reduced pressure The residue was distilled under reduced pressure

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

Procedure: Obtained by operating as in example 87a, from 19.7 g (195 mmoles) of diisopropylamine, 122 ml (195 mmoles) of a 1.6M solution of n-butyllithium in hexane, 45 ml of 1,3-dimethylimidazolidin-2-one, 21.8 g of 2,2,3,3-tetramethylcyclopropanecarbonitrile (prepared according to patent FR 2,479,192), 51.9 g (180.5 mmoles) of the compound prepared in example 26a in 295 ml tetrahydrofuran. After distillation, there is obtained 20 g (yield=44.0%) of a thick yellow oil. b.p.0.8 =185°-205° C. Obtained After distillation

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

Procedure: 9.15 ml of a cyclohexane solution of 1.75M of butyllithium were added with stirring under an inert atmosphere at -30° to -40° C. to a mixture of 2.49 ml of diisopropylamine and 5 ml of tetrahydrofuran and after 10 minutes of contact, the mixture was cooled to -60° to -70° C. A mixture of 4.068 g of 4-tolyl sulfonyl-4,3,3,-trimethyl-pentanenitrile in 15 ml of tetrahydrofuran were added to the mixture over 5 minutes and the mixture was stirred at -60° to -70° C. for 10 minutes after which the temperature was allowed to rise to 20° to 25° C. The mixture was stirred for one hour and was then poured into an iced aqueous saturated monosodium phosphate solution. The mixture was extracted with n-pentane and the organic phase was dried and evaporated to dryness under reduced pressure. The residue was distilled under reduced pressure to obtain 1.064 g of pure 2,2,3,3-tetramethyl-cyclopropane-carbonitrile with a boiling point of 58°-60° C. at 12-14 mm Hg and a melting point of 17° C. the mixture was cooled to -60° to -70° C were added to the mixture over 5 minutes to rise to 20° to 25° C The mixture was stirred for one hour The mixture was extracted with n-pentane the organic phase was dried evaporated to dryness under reduced pressure The residue was distilled under reduced pressure

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

Procedure: 9.15 ml of a cyclohexane solution of 1.75M of butyllithium were added with stirring under an inert atmosphere at -30° to -40° C. to a mixture of 2.49 ml of diisopropylamine and 5 ml of tetrahydrofuran and after 10 minutes of contact, the mixture was cooled to -60° to -70° C. A mixture of 4.068 g of 4-tolyl sulfonyl-4,3,3-trimethyl-pentanenitrile in 15 ml of tetrahydrofuran were added to the mixture over 5 minutes and the mixture was stirred at -60° to -70° C. for 10 minutes after which the temperature was allowed to rise to 20° to 25° C. The mixture was stirred for one hour and was then poured into an iced aqueous saturated monosodium phosphate solution. The mixture was extracted with n-pentane and the organic phase was dried and evaporated to dryness under reduced pressure. The residue was distilled under reduced pressure to obtain 1.064 g of pure 2,2,3,3-tetramethyl-cyclopropane-carbonitrile with a boiling point of 58°-60° C. at 12-14 mm Hg and a melting point of 17° C. the mixture was cooled to -60° to -70° C were added to the mixture over 5 minutes to rise to 20° to 25° C The mixture was stirred for one hour The mixture was extracted with n-pentane the organic phase was dried evaporated to dryness under reduced pressure The residue was distilled under reduced pressure

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

Procedure: Obtained by operating as in example 87a, from 19.7 g (195 mmoles) of diisopropylamine, 122 ml (195 mmoles) of a 1.6M solution of n-butyllithium in hexane, 45 ml of 1,3-dimethylimidazolidin-2-one, 21.8 g of 2,2,3,3-tetramethylcyclopropanecarbonitrile (prepared according to patent FR 2,479,192), 51.9 g (180.5 mmoles) of the compound prepared in example 26a in 295 ml tetrahydrofuran. After distillation, there is obtained 20 g (yield=44.0%) of a thick yellow oil. b.p.0.8 =185°-205° C. Obtained After distillation