Dimethyl Sulfate → HCID 54390956、化合物

HRID 1720562ノート

反応式

HRID 1720562 の反応式
[OH-].[Na+].[N:3]([O:5][CH2:6]CCC)=O.[CH3:10][C:11]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][C:12]=1[O:13][CH2:14][C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[CH2:17][C:18]#[N:19].S(OC)(OC)(=O)=O>O.C1(C)C=CC=CC=1.CC(C)=O>[CH3:10][C:11]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][C:12]=1[O:13][CH2:14][C:15]1[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=1[C:17]([C:18]#[N:19])=[N:3][O:5][CH3:6]

参加物

8

反応物 4

HCID 6497Dimethyl SulfateHCID 10996Butyl nitriteHCID 14798Sodium Hydroxide2 回HCID 11118528HCID 11118528、化合物

生成物 1

HCID 54390956HCID 54390956、化合物収率 87.7%

試薬・触媒・溶媒 3

HCID 180Acetone溶媒HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

95% Sodium hydroxide (0.32 g, 7.5 mmol), acetone (5 ml) and butyl nitrite (0.62 g, 6 mmol) were added to 2-(2,5-dimethylphenoxymethyl)benzyl cyanide (1.26 g, 5 mmol). The mixture was stirred at room temperature for 2 hours. Dimethyl sulfate (0.95 g, 7.5 mmol) was added, and the mixture was stirred under ice-cooling for 10 minutes and at room temperature for 1 hour. After completion of the reaction, toluene (10 ml) and 1N aqueous sodium hydroxide solution (10 ml) were added, and the mixture was stirred at room temperature for 1 hour. After stirring, water (100 ml) was added. The mixture was extracted with ether (100 ml), dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (ethyl acetate/n-hexane) to give 2-(2,5-dimethylphenoxymethyl)-α-methoxyiminobenzyl cyanide (1.29 g, Yield: 87.6%, E/Z=13/87).

後処理

  1. stirringthe mixture was stirred under ice-
  2. temperaturecooling for 10 minutes and at room temperature for 1 hour
  3. additionwere added
  4. stirringthe mixture was stirred at room temperature for 1 hour
  5. stirringAfter stirring
  6. extractionThe mixture was extracted with ether (100 ml)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting residue was purified by silica gel chromatography (ethyl acetate/n-hexane)

出典と根拠

ORDレコード
ord-b8b604332f514944b1ec921d811b96d8
出典データセット
uspto-grants-1996_04
特許番号
US05506358

反応ノート

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