Ethyl Acetate → HCID 68407746, 화합물

HRID 1920221노트

반응식

HRID 1920221 반응식
[CH3:1][CH:2]1[CH2:7][C:6]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[N+:14]([O-:16])=[O:15])=[CH:5]C=C1.C1C(=O)N([Br:24])C(=O)C1.C([O:28][CH2:29][CH3:30])(=O)C>C1COCC1.O>[Br:24][CH:30]1[CH:29]([OH:28])[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[N+:14]([O-:16])=[O:15])[CH2:7][CH:2]1[CH3:1]

참가 물질

6

반응물 3

HCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 59226560HCID 59226560, 화합물

생성물 1

HCID 68407746HCID 68407746, 화합물수율 80%

시약·촉매·용매 2

HCID 962Water용매2회HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 4-(5-methylcyclohexa-1,3-dienyl)-3-nitropyridine (1.0 equiv.) in THF and water (1:1, 0.13M) was added NBS (1.5 equiv.) and the reaction was stirred at room temperature for 30 min. Upon completion, ethyl acetate and water were added to the reaction, the organic phase was dried with brine, then sodium sulfate, filtered, and concentrated. The crude material was purified via silica gel column chromatography eluting with ethyl acetate and hexanes (1:1) to give (+/−)-6-bromo-5-methyl-3-(3-nitropyridin-4-yl)cyclohex-2-enol as a yellow oil in 80% yield. LC/MS=315.0/313.0 (M+H), LC=2.966 min.

후처리

  1. dry with materialthe organic phase was dried with brine
  2. filtrationsodium sulfate, filtered
  3. concentrationconcentrated
  4. customThe crude material was purified via silica gel column chromatography
  5. washeluting with ethyl acetate and hexanes (1:1)

출처 및 근거

ORD 기록
ord-6bc22a63277f470daed66dcd78e62415
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08168794B2

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