Toluene → HCID 13671387、化合物

HRID 1380906ノート

反応式

HRID 1380906 の反応式
[C:1]1([CH3:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:8]([C:15]1[N:20]=[C:19]([CH:21]=[O:22])[CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C1(C)C([S:29](Cl)(=[O:31])=[O:30])=CC=CC=1.[C-:34]#[N:35].[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[S:29]([C:4]1[CH:5]=[CH:6][C:1]([CH3:7])=[CH:2][CH:3]=1)([O:22][CH:21]([C:34]#[N:35])[C:19]1[CH:18]=[CH:17][CH:16]=[C:15]([O:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:20]=1)(=[O:31])=[O:30]

参加物

7

反応物 4

HCID 1140TolueneHCID 8623o-Toluenesulfonyl chlorideHCID 8929Sodium Cyanide2 回HCID 129410066-Phenoxypyridine-2-carbaldehyde

生成物 1

HCID 13671387HCID 13671387、化合物

試薬・触媒・溶媒 2

HCID 70681Tetrabutylammonium Chloride触媒HCID 962Water溶媒2 回

反応条件

温度
0 °C

実験手順

A 25 ml roundbottom flask equipped with a dropping funnel, thermometer and stirring bar was charged with 6 ml of toluene, 5 g of 6-phenoxy-2-pyridinecarboxaldehyde and 4.41 g of toluenesulfonyl chloride. The dropping funnel was charged with 10 ml of water, 1.2 g of sodium cyanide and 50 mg of tetrabutylammonium chloride. The solution was cooled to 0° C. and the sodium cyanide solution was added dropwise over 25 minutes. The temperature was controlled to about 4° C. as the solution turned pink and exothermic. The solution was allowed to stand at 4° C. for 1/2 hour. The reaction mixture was poured into 150 ml of water and extracted with four 75 ml portions of diethyl ether. The combined extract was washed with two 150 ml portions of water, dried (MgSO4) and stripped to give a crude amber oil. The crude oil product was chromatographed using 1:1 methylene chloride/hexane as eluent to yield 4.2 g of the desired product as an amber oil.

後処理

  1. customA 25 ml roundbottom flask equipped with a dropping funnel
  2. customwas controlled to about 4° C. as the solution
  3. extractionextracted with four 75 ml portions of diethyl ether
  4. extractionThe combined extract
  5. washwas washed with two 150 ml portions of water
  6. dry with materialdried (MgSO4)
  7. customto give a crude amber oil
  8. customThe crude oil product was chromatographed

出典と根拠

ORDレコード
ord-737725d070244fef87bf014fbc34220d
出典データセット
uspto-grants-1986_04
特許番号
US04584304

反応ノート

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