Diisopropylamine → Tetramethylcyclopropane-1-carbonitrile

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.

1. temperaturethe mixture was cooled to -60° to -70° C
2. additionwere added to the mixture over 5 minutes
3. customto rise to 20° to 25° C
4. stirringThe mixture was stirred for one hour
5. extractionThe mixture was extracted with n-pentane
6. customthe organic phase was dried
7. customevaporated to dryness under reduced pressure
8. distillationThe residue was distilled under reduced pressure

ORDレコード

ord-23be0151a03f4375993e99a3220bfecf

出典データセット

uspto-grants-1985_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US04501704