Phosphorus oxychloride → 4-(4-chloro-2-pyridyl)-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile
반응식
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH3:13])([CH3:12])[CH2:9][CH:8]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N+:15]=3[O-])[C:7]=2[CH:21]=1)#[N:2].P(Cl)(Cl)([Cl:24])=O>>[Cl:24][C:18]1[CH:17]=[CH:16][N:15]=[C:14]([CH:8]2[C:7]3[CH:21]=[C:3]([C:1]#[N:2])[CH:4]=[CH:5][C:6]=3[O:11][C:10]([CH3:13])([CH3:12])[CH2:9]2)[CH:19]=1참가 물질
반응 조건
- 온도
- 80 °C
실험 절차
1 g of 2-(6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-yl)pyridine N-oxide was dissolved in 15 ml of phosphorus oxychloride, heated at 80° C. for 2 hours and allowed to cool to room temperature overnight. The phosphorus oxychloride was removed in vacuo and the residue was taken up in sodium bicarbonate solution and ethyl acetate. The aqueous phase was extracted several times with ethyl acetate and the combined ethyl acetate solutions were dried over sodium sulphate and evaporated. The residue was chromatographed on silica gel. Elution with ethyl acetate/petroleum ether (1:4) gave 271 mg of 4-(6-chloro-2-pyridyl)-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile and elution with ethyl acetate/petroleum ether (1:2) gave 170 mg of 4-(4-chloro-2-pyridyl)-3,4-dihydro-2,2-dimethyl-2H-1 -benzopyran-6carbonitrile.
후처리
- temperatureto cool to room temperature overnight
- customThe phosphorus oxychloride was removed in vacuo
- extractionThe aqueous phase was extracted several times with ethyl acetate
- dry with materialthe combined ethyl acetate solutions were dried over sodium sulphate
- customevaporated
- customThe residue was chromatographed on silica gel
- washElution with ethyl acetate/petroleum ether (1:4)
- customgave
- wash271 mg of 4-(6-chloro-2-pyridyl)-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile and elution with ethyl acetate/petroleum ether (1:2)
출처 및 근거
- ORD 기록
- ord-1de9ff71d42a4fb7aa4b8d2d6be941d0
- 출처 데이터셋
- uspto-grants-1992_06
- 특허 번호
- US05118694
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