Dimethylformamide → 3-Chloro-3-[3-chloro-4-(3,3,5,5-tetramethylcyclohexyl)phenyl]propenal

HRID 1071922ノート

反応式

HRID 1071922 の反応式
C(Cl)(=O)C([Cl:4])=O.CN(C)[CH:9]=[O:10].[Cl:12][C:13]1[CH:14]=[C:15]([C:29](=O)[CH3:30])[CH:16]=[CH:17][C:18]=1[CH:19]1[CH2:24][C:23]([CH3:26])([CH3:25])[CH2:22][C:21]([CH3:28])([CH3:27])[CH2:20]1.[O-]CC.[Na+]>ClCCl>[Cl:4][C:29]([C:15]1[CH:16]=[CH:17][C:18]([CH:19]2[CH2:24][C:23]([CH3:26])([CH3:25])[CH2:22][C:21]([CH3:28])([CH3:27])[CH2:20]2)=[C:13]([Cl:12])[CH:14]=1)=[CH:30][CH:9]=[O:10]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 2723922Sodium ethoxideHCID 223904251-[3-Chloro-4-(3,3,5,5-tetramethylcyclohexyl)phenyl]ethanone

生成物 1

HCID 572145173-Chloro-3-[3-chloro-4-(3,3,5,5-tetramethylcyclohexyl)phenyl]propenal

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

3.51 ml of oxalyl chloride are added dropwise at a temperature of between −5° C. and 2° C. to a solution of 3.72 ml of dimethylformamide and 20 ml of anhydrous dichloromethane and the reaction mixture is then stirred at room temperature for 30 minutes. 3.92 g of 1-[3-chloro-4-(3,3,5,5-tetramethylcyclohexyl)phenyl]ethanone (compound V.6) dissolved in 10 ml of dichloromethane are then added rapidly, after which the reaction mixture is stirred at room temperature for 12 hours. The reaction mixture is poured into a water/ice mixture and 20 ml of aqueous 2.84 M sodium ethoxide solution are then added. The resulting mixture is washed with 50 ml of sodium hydrogen carbonate solution and 50 ml of water, the phases are separated after settling has taken place, the organic phase is dried over magnesium sulphate and the solvents are evaporated off under reduced pressure. The oil obtained is purified by chromatography on a column of silica gel, eluting with a 97/3 (v/v) cyclohexane/ethyl acetate mixture.

後処理

  1. additionare then added rapidly
  2. stirringafter which the reaction mixture is stirred at room temperature for 12 hours
  3. additionare then added
  4. washThe resulting mixture is washed with 50 ml of sodium hydrogen carbonate solution and 50 ml of water
  5. customthe phases are separated after settling
  6. dry with materialthe organic phase is dried over magnesium sulphate
  7. customthe solvents are evaporated off under reduced pressure
  8. customThe oil obtained
  9. customis purified by chromatography on a column of silica gel
  10. washeluting with a 97/3 (v/v) cyclohexane/ethyl acetate mixture

出典と根拠

ORDレコード
ord-6cc9601a5bd141749032081270bcee4c
出典データセット
uspto-grants-2005_06
特許番号
US06908914B1

反応ノート

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