Ethyl 6-(p-chlorophenylsulfonamido)-2-[3-(3pyridyl)propyl]-hexanoate → 6-(p-Chlorophenylsulfonamido)-2-[3-(3-pyridyl)propyl]-hexanal

HRID 465523노트

반응식

HRID 465523 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([CH2:22][CH2:23][CH2:24][C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)[C:17](OCC)=[O:18])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C>C(Cl)Cl.C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH:16]([CH2:22][CH2:23][CH2:24][C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)[CH:17]=[O:18])(=[O:10])=[O:9])=[CH:4][CH:3]=1

참가 물질

5

반응물 2

HCID 10004033Ethyl 6-(p-chlorophenylsulfonamido)-2-[3-(3pyridyl)propyl]-hexanoateHCID 21225700Diisobutylaluminumhydride

생성물 1

HCID 102509236-(p-Chlorophenylsulfonamido)-2-[3-(3-pyridyl)propyl]-hexanal

시약·촉매·용매 2

HCID 1140Toluene용매HCID 6344Dichloromethane용매

실험 절차

A solution of 3.5 g (7.7 mmol) of ethyl 6-(p-chlorophenylsulfonamido)-2-[3-(3-pyridyl)propyl]-hexanoate (example 2) in 105 ml methylene chloride is cooled to -78° and to it is added slowly added 15.2 ml (23.6 mmol) of 1.53M solution of diisobutylaluminium hydride in toluene. The solution is stirred at -78° for 10 min and then quenched by slow addition of 10.8 ml methanol. The solution is then allowed to warm to 0° by the removal of the cold bath, and then 350 ml of ether is added followed by 10.8 ml of saturated brine and 7.7 g finely powdered anhydrous sodium sulfate. The cloudy suspension is stirred vigorously at room temperature overnight. The salts are filtered off and washed with methylene chloride (10×20 ml). The filtrate is evaporated to give 6-(p-chlorophenylsulfonamido)-2-[3-(3-pyridyl)propyl]-hexanal.

후처리

  1. customquenched by slow addition of 10.8 ml methanol
  2. temperatureto warm to 0° by the removal of the cold bath
  3. addition350 ml of ether is added
  4. stirringThe cloudy suspension is stirred vigorously at room temperature overnight
  5. filtrationThe salts are filtered off
  6. washwashed with methylene chloride (10×20 ml)
  7. customThe filtrate is evaporated

출처 및 근거

ORD 기록
ord-7260f01e725d41b5b9a1ae1e527e5697
출처 데이터셋
uspto-grants-1992_10
특허 번호
US05153214

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