Isopropyl iodide → HCID 59442121、化合物

HRID 1014182ノート

反応式

HRID 1014182 の反応式
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([C:18]2[CH2:23][NH:22][CH2:21][CH2:20][CH:19]=2)[CH:12]=[CH:13][C:14]=1[N+:15]([O-:17])=[O:16].I[CH:25]([CH3:27])[CH3:26]>C(#N)C>[CH3:26][CH:25]([N:22]1[CH2:23][C:18]([C:11]2[CH:12]=[CH:13][C:14]([N+:15]([O-:17])=[O:16])=[C:9]([O:8][CH3:7])[CH:10]=2)=[CH:19][CH2:20][CH2:21]1)[CH3:27]

参加物

5

反応物 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 59441667HCID 59441667、化合物

生成物 1

HCID 59442121HCID 59442121、化合物収率 80%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
85 °C

実験手順

To a pressure vessel containing acetonitrile (40 mL) and potassium carbonate (4.0 g, 29.2 mmol) was added 5-[3-(methyloxy)-4-nitrophenyl]-1,2,3,6-tetrahydropyridine (1.7 g, 7.3 mmol) and 2-iodopropane (1.85 g, 10.9 mmol). The reaction was stirred at 85° C. overnight. After removal of the solvent under reduced pressure the residue was diluted with ethyl acetate (30 mL) and washed with water (40 mL). After partitioning and extraction of the aqueous layer (Ethyl acetate 2×15 mL), the organic layer was dried over sodium sulfate, filtered, concentrated and purified via chromatography on SiO2 to afford 1-(1-methylethyl)-5-[3-(methyloxy)-4-nitrophenyl]-1,2,3,6-tetrahydropyridine (1.6 g, 80% yield.) ESIMS (M+H)+=277.1.

後処理

  1. customAfter removal of the solvent under reduced pressure the residue
  2. additionwas diluted with ethyl acetate (30 mL)
  3. washwashed with water (40 mL)
  4. customAfter partitioning
  5. extractionextraction of the aqueous layer (Ethyl acetate 2×15 mL)
  6. dry with materialthe organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. custompurified via chromatography on SiO2

出典と根拠

ORDレコード
ord-491667614fe141419a426ae075855ea9
出典データセット
uspto-grants-2011_07
特許番号
US07981903B2

反応ノート

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