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

HRID 1018807노트

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HRID 1018807 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f8dedd069e3949489c2edd6a2d370b42
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06482986B1

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