Methyl iodide → 2-[3-(2-Methylhexanoyl) phenoxymethyl]quinoline

HRID 414835ノート

反応式

HRID 414835 の反応式
[C:1]([C:8]1[CH:9]=[C:10]([CH:23]=[CH:24][CH:25]=1)[O:11][CH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1)(=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[H-].[Na+].[CH3:28]I>C1COCC1>[CH3:28][CH:2]([CH2:3][CH2:4][CH2:5][CH3:6])[C:1]([C:8]1[CH:9]=[C:10]([CH:23]=[CH:24][CH:25]=1)[O:11][CH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=1)=[O:7]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 13560729HCID 13560729、化合物

生成物 1

HCID 143491272-[3-(2-Methylhexanoyl) phenoxymethyl]quinoline

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of the ketone, 2-(3-hexanoylphenoxymethyl)quinoline (prepared from 3-hexanoylphenol and 2-chloromethyl quinoline)(6 g, 0.018 mol) in dry THF (25 ml) was added slowly to a mildly refluxing suspension of sodium hydride (1.3 g, 0.054 mol) in dry THF (75 ml) containing excess methyl iodide (10.3 g, 0.073 mol) After the addition of the ketone was complete (30 min.), the reaction mixture was refluxed for 4 hours. After cooling the mixture to room temperature, excess NaH was destroyed by adding methanol. All volatiles were removed at the rotary evaporator and the residue was taken up in ethyl acetate. The organic extract was washed with water and brine, and dried over anhydrous magnesium sulfate. Upon removal of all solvent, the mono-methylated eetone (2-[3-(2-methylhexanoyl) phenoxymethyl]quinoline, was obtained as a yellow oil weighing 8 g.

後処理

  1. temperaturea mildly refluxing
  2. custom(30 min.)
  3. temperaturethe reaction mixture was refluxed for 4 hours
  4. customexcess NaH was destroyed
  5. additionby adding methanol
  6. customAll volatiles were removed at the rotary evaporator
  7. extractionThe organic extract
  8. washwas washed with water and brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customUpon removal of all solvent

出典と根拠

ORDレコード
ord-0d554e52cc8348f0acce04e90bb67428
出典データセット
uspto-grants-1988_12
特許番号
US04794188

反応ノート

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