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HRID 274252생성일: 2026년 10월 25일

Ethyl butyrate → 5-[(2'-Cyanobiphenyl-4-yl)methyl]-4,6-dioxononane

https://huagongshe.com/reaction/274252

반응식

참여 물질

역할이름HCID투입량
반응물Ethyl butyrateHCID 7762—
반응물2-PentanoneHCID 7895—
반응물Lithium amideHCID 24532—
반응물Sodium hydrideHCID 24758—
반응물4,6-NonanedioneHCID 26454—
반응물4'-(Bromomethyl)-2-cyanobiphenylHCID 1501912—
용매DimethylformamideHCID 6228—
생성물5-[(2'-Cyanobiphenyl-4-yl)methyl]-4,6-dioxononaneHCID 20092863104.6%

반응 단계

15.6 g of 4,6-dioxononane, prepared from methyl propyl ketone and ethyl butyrate in the presence of lithium amide (according to CA 42 : 4129 f), are dissolved in 160 ml of anhydrous DMF. 4 g of 60% NaH are added in portions. When the exothermic effect has subsided, the mixture is cooled to room temperature and a solution of 27.2 g of 4'-bromomethyl-2-cyanobiphenyl, prepared in Example 4, in 90 ml of DMF is introduced dropwise. The mixture is stirred for 30 min at room temperature and then heated at 60° C. for 2 h. It is concentrated under vacuum and the concentrate is taken up in a water/dichloromethane mixture and acidified with a dilute solution of HCl. After decantation, the aqueous phase is extracted twice with dichloromethane. The organic phases are washed with water, dried and then concentrated to give 36.3 g of an oil, which is purified by chromatography twice in succession (eluent: chloroform, then cyclohexane 90%/ethyl acetate 10% respectively) to give a solid identified by NMR as being the enol tautomer melting at 105° C., and an oil corresponding to the diketone tautomeric form.

출처 및 근거

DOI10.6084/m9.figshare.5104873.v1
특허 번호US05389632
출처 데이터셋uspto-grants-1995_02
ORD IDord-93a37d520490420fbbdb674b463811c7
출처 메모uspto-grants-1995_02