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Iodoethane → 1-Ethyl-6-methoxy-2-oxo-1,2,3,4-tetrahydro-quinoline-7-carbaldehyde

HRID 1243982
ノート
印刷プレビュー

反応式

HRID 1243982 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[CH:13]=[O:14])[NH:9][C:8](=[O:15])[CH2:7][CH2:6]2.[CH3:16][C:17](C)([O-])C.[K+].C(I)C>C1COCC1.C(=O)(O)[O-].[Na+]>[CH2:16]([N:9]1[C:10]2[C:5](=[CH:4][C:3]([O:2][CH3:1])=[C:12]([CH:13]=[O:14])[CH:11]=2)[CH2:6][CH2:7][C:8]1=[O:15])[CH3:17]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 6340IodoethaneHCID 101251496-Methoxy-2-oxo-1,2,3,4-tetrahydro-quinoline-7-carbaldehydeHCID 23665647Potassium tert-butoxide

生成物 1

HCID 219317301-Ethyl-6-methoxy-2-oxo-1,2,3,4-tetrahydro-quinoline-7-carbaldehyde

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 516892
Sodium Bicarbonate
溶媒

反応条件

温度
0 °C

実験手順

6-Methoxy-2-oxo-1,2,3,4-tetrahydro-quinoline-7-carbaldehyde (preparation 3) 60 mg (0.293 mmol) was dissolved in 5 ml of anhydrous THF and the solution was cooled to 0° C. The reaction mixture was treated with 33 mg (0.293 mmol) of potassium t-butoxide whereupon it became yellow in color. After stirring for 30 minutes, the mixture was treated with 23 μl (0.293 mmol) ethyl iodide and slowly warmed to room temperature while stirring for 16 hours (h). The reaction mixture was diluted with saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate. The organic phase was dried over sodium sulfate and concentrated to an oil. The residue was chromatographed on silica gel eluting with 6/4 ethyl acetate/hexane to afford 34 mg (40%) as a white solid. MS APCI m/e 234 (p+1)

後処理

  1. temperatureslowly warmed to room temperature
  2. stirringwhile stirring for 16 hours (h)
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. concentrationconcentrated to an oil
  6. customThe residue was chromatographed on silica gel eluting with 6/4 ethyl acetate/hexane
  7. customto afford 34 mg (40%) as a white solid

出典と根拠

ORDレコード
ord-038ec84659ca4c1caba32b2f8fe6b238
出典データセット
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07119207B2

反応ノート

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