p-Toluenesulfonic acid → HCID 59226521、化合物

HRID 73577ノート

反応式

HRID 73577 の反応式
[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

参加物

6

反応物 4

HCID 6101p-Toluenesulfonic acidHCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 59226486HCID 59226486、化合物

生成物 1

HCID 59226521HCID 59226521、化合物収率 27%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-00be404b76784758aac5a62345c1364d
出典データセット
uspto-grants-2014_09
特許番号
US08829193B2

反応ノート

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