4-Toluenesulfonyl chloride → (5-Ethyl-2-pyridyl)ethane p-toluenesulfonate
Reaction equation
[OH-].[Na+].[CH2:3]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]([OH:13])[CH3:12])=[N:9][CH:10]=1)[CH3:4].[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1>O.O1CCCC1>[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20]([OH:13])(=[O:22])=[O:21])=[CH:16][CH:15]=1.[CH2:3]([C:5]1[CH:6]=[CH:7][C:8]([CH2:11][CH3:12])=[N:9][CH:10]=1)[CH3:4]Participants
Procedure
7.1 g of sodium hydroxide was dissolved in 33 ml of water, and 7.6 g of (5-ethyl-2-pyridyl)ethanol was dissolved in 33 ml of tetrahydrofuran. Both solutions were mixed and cooled. To the resultant solution was added dropwise gradually at 0° C. a solution of 11.7 g of p-toluenesulfonyl chloride in 51 ml of tetrahydrofuran, followed by stirring for 2 hours at the same temperature. To the reaction mixture was added ice water. The mixture was extracted twice with 100 ml each of methylene chloride. The extracted organic layers are combined. The resultant organic layer was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, whereby 14.4 g of (5-ethyl-2-pyridyl)ethane p-toluenesulfonate was obtained as a pale yellow oily product.
Workup
- additionBoth solutions were mixed
- temperaturecooled
- extractionThe mixture was extracted twice with 100 ml each of methylene chloride
- washThe resultant organic layer was washed with water
- dry with materialdried over anhydrous sodium sulfate
- distillationThe solvent was distilled off under reduced pressure
Sources & evidence
- ORD record
- ord-e41048f6d0ef4cb9afce8798ae72002a
- Source dataset
- uspto-grants-1996_09
- Patent number
- US05554758
Reaction notes
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