참여 물질
| 역할 | 이름 | HCID | 투입량 |
|---|
| 반응물 | Ethyl butyrate | HCID 7762 | — |
| 반응물 | 2-Pentanone | HCID 7895 | — |
| 반응물 | Lithium amide | HCID 24532 | — |
| 반응물 | Sodium hydride | HCID 24758 | — |
| 반응물 | 4,6-Nonanedione | HCID 26454 | — |
| 반응물 | 4'-(Bromomethyl)-2-cyanobiphenyl | HCID 1501912 | — |
| 용매 | Dimethylformamide | HCID 6228 | — |
| 생성물 | 5-[(2'-Cyanobiphenyl-4-yl)methyl]-4,6-dioxononane | HCID 20092863 | 104.6% |
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
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| 특허 번호 | US05389632 |
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| 출처 데이터셋 | uspto-grants-1995_02 |
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| ORD ID | ord-93a37d520490420fbbdb674b463811c7 |
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| 출처 메모 | uspto-grants-1995_02 |
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