Ethyl 6-(p-chlorophenylsulfonamido)-2-[3-(3pyridyl)propyl]-hexanoate → 6-(p-Chlorophenylsulfonamido)-2-[3-(3-pyridyl)propyl]-hexanal
Reaction equation
[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]=1Participants
Procedure
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.
Workup
- customquenched by slow addition of 10.8 mL methanol
- temperatureto warm to 0° by the removal of the cold bath
- addition350 mL of ether is added
- stirringThe cloudy suspension is stirred vigorously at room temperature overnight
- filtrationThe salts are filtered off
- washwashed with methylene chloride (10×20 mL)
- customThe filtrate is evaporated
Sources & evidence
- ORD record
- ord-5b7f6fe356ac4dfda5517d7d1c149306
- Source dataset
- uspto-grants-1991_06
- Patent number
- US05025025
Reaction notes
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