p-Toluenesulfonic acid → HCID 59226521, 화합물

HRID 73577노트

반응식

HRID 73577 반응식
[N+:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[C:10]1[CH2:15][CH2:14][CH2:13][CH:12](O)[CH:11]=1)([O-:3])=[O:2].O1CCOCC1.CC1C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>C(OCC)(=O)C>[C:10]1([C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[N+:1]([O-:3])=[O:2])[CH2:15][CH2:14][CH:13]=[CH:12][CH:11]=1

참가 물질

6

반응물 4

HCID 6101p-Toluenesulfonic acidHCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 59226486HCID 59226486, 화합물

생성물 1

HCID 59226521HCID 59226521, 화합물수율 27%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

To a solution of 3-(3-nitropyridin-4-yl)cyclohex-2-enol (1.0 equiv.) was added dioxane (0.18M) and p-TSA (1.1 equiv.). The solution was heated to 100° C. for 4 h. Cooled to room temperature, worked up with sat. NaHCO3 and ethyl acetate, the organic phase was dried with Na2SO4 and concentrated. The crude was purified via silica gel column chromatography eluting with 100% DCM to give 4-(cyclohexa-1,3-dienyl)-3-nitropyridine as a yellow oil (27% yield). LCMS (m/z): 203.1 (MH+), LC Rt=3.53 min, 1H-NMR (CDCl3): 9.02 (s, 1H), 8.70 (d, J=5.3, 1H), 7.30 (d, J=5.3, 1H), 6.15-6.17 (m, 1H), 6.02-6.11 (m, 2H), 2.35-2.38 (m, 4H).

후처리

  1. temperatureCooled to room temperature
  2. dry with materialthe organic phase was dried with Na2SO4
  3. concentrationconcentrated
  4. customThe crude was purified via silica gel column chromatography
  5. washeluting with 100% DCM

출처 및 근거

ORD 기록
ord-00be404b76784758aac5a62345c1364d
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829193B2

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