Hexane → HCID 21973146、化合物

HRID 1814825ノート

反応式

HRID 1814825 の反応式
[Cl-:1].[NH4+:2].C[Al](C)C.CCCCCC.[CH2:13]([O:20][C:21]1[CH:22]=[CH:23][C:24]([O:29][CH2:30][CH3:31])=[C:25]([CH:28]=1)[C:26]#[N:27])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1(C)C=CC=CC=1.ClCCl>[ClH:1].[CH2:13]([O:20][C:21]1[CH:28]=[C:25]([C:24]([O:29][CH2:30][CH3:31])=[CH:23][CH:22]=1)[C:26]([NH2:2])=[NH:27])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

参加物

7

反応物 4

HCID 8058HexaneHCID 25517Ammonium ChlorideHCID 16682925TrimethylaluminumHCID 219731695-Benzyloxy-2-ethoxybenzonitrile

生成物 1

HCID 21973146HCID 21973146、化合物

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
2.5 °C

実験手順

46.46 g of ammonium chloride (868.5 mol) are suspended in 650 ml of toluene, and the mixture is cooled to 0-5° C. Trimethylaluminum is added dropwise as a 2M solution in hexane (445 ml, 888.3 mmol), and the mixture is then stirred at room temperature until the evolution of gas has ceased. 5-Benzyloxy-2-ethoxybenzonitrile (100 g, 394.8 mmol) (example 32A) is added, and the mixture is stirred at 80° C. overnight. The cooled reaction mixture is, with ice-cooling, added to a suspension of 200 g of silica gel and 2 l of dichloromethane, and the mixture is stirred for 30 min. The mixture is filtered off with suction and the filter cake is washed with methanol. The organic phases are combined and concentrated. The resulting residue is triturated using a mixture of dichloromethane/methanol 9:1, filtered and concentrated using a rotary evaporator. The residue is then triturated with ether, and the colorless solid is filtered off with suction.

後処理

  1. stirringthe mixture is stirred at 80° C. overnight
  2. customThe cooled reaction mixture
  3. temperaturecooling
  4. stirringthe mixture is stirred for 30 min
  5. filtrationThe mixture is filtered off with suction
  6. washthe filter cake is washed with methanol
  7. concentrationconcentrated
  8. customThe resulting residue is triturated
  9. additiona mixture of dichloromethane/methanol 9:1
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customa rotary evaporator
  13. customThe residue is then triturated with ether
  14. filtrationthe colorless solid is filtered off with suction

出典と根拠

ORDレコード
ord-d58d186105994bd6961aacecc5b80d80
出典データセット
uspto-grants-2005_04
特許番号
US06878708B2

反応ノート

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