Triethylamine → HCID 19780237、化合物

HRID 2081587ノート

反応式

HRID 2081587 の反応式
C[Si]([C:5]#[N:6])(C)C.[Cl:7][C:8]1[CH:21]=[CH:20][CH:19]=[CH:18][C:9]=1[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N+:12]=1[O-].C(N(CC)CC)C>C(#N)C>[Cl:7][C:8]1[CH:21]=[CH:20][CH:19]=[CH:18][C:9]=1[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:5]#[N:6])[N:12]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 82115Trimethylsilyl cyanideHCID 19780238HCID 19780238、化合物

生成物 1

HCID 19780237HCID 19780237、化合物収率 35%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

Trimethylsilyl cyanide (36.15 g, 48.6 ml, 0.36 moles) was added dropwise to a solution of 2-(o-chlorobenzyl)-pyridine-N-oxide (32.0 g, 0.15 moles) and triethylamine (22.13 g, 30.5 ml, 0.22 moles) in acetonitrile (100 ml) at 20° C. under a nitrogen atmosphere. After complete addition the reaction mixture was heated under reflux for 48 hours, cooled to room temperature and partitioned between methylene chloride and saturated sodium bicarbonate solution. The organic layer was washed with water and saturated sodium chloride solution and was then dried over anhydrous magnesium sulphate. Removal of the solvent gave an orange brown oil which was purified by column chromatography (silica gel eluted with hexane:ethyl acetate 4:1) to give 2-(o-chlorobenzyl)-6-cyanopyridine (11.5 g, 35%) as a pale yellow oil.

後処理

  1. additionAfter complete addition the reaction mixture
  2. temperaturewas heated
  3. temperatureunder reflux for 48 hours
  4. custompartitioned between methylene chloride and saturated sodium bicarbonate solution
  5. washThe organic layer was washed with water and saturated sodium chloride solution
  6. dry with materialwas then dried over anhydrous magnesium sulphate
  7. customRemoval of the solvent
  8. customgave an orange brown oil which
  9. customwas purified by column chromatography (silica gel eluted with hexane:ethyl acetate 4:1)

出典と根拠

ORDレコード
ord-97d5f16fc7044fb0bb3bbebaa1966990
出典データセット
uspto-grants-1993_02
特許番号
US05185339

反応ノート

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