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

HRID 1494067ノート

反応式

HRID 1494067 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒

実験手順

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 15.2 mL (23.6 mmol) of 1.53M solution of diisobutylaluminum hydride in toluene. The solution is stirred at -78° for 10 minutes 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.

後処理

  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

出典と根拠

ORDレコード
ord-5b7f6fe356ac4dfda5517d7d1c149306
出典データセット
uspto-grants-1991_06
特許番号
US05025025

反応ノート

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