Water → 2-(5-Ethylpyridin-2-yl)ethyl methanesulfonate
Reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:9](O)[CH3:10])=[N:7][CH:8]=1)[CH3:2].C(N(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21].[OH2:24]>C(Cl)Cl>[CH3:19][S:20]([O:22][CH2:10][CH2:9][C:6]1[CH:5]=[CH:4][C:3]([CH2:1][CH3:2])=[CH:8][N:7]=1)(=[O:24])=[O:21]Participants
Procedure
In 800 ml of methylene chloride was dissolved 80 g of (5-ethyl-2-pyridyl)ethanol, to which was added 55 g of triethylamine. To this mixture was added dropwise gradually 73.2 g of methanesulfonyl chloride while stirring under cooling, and the mixture was stirred for 3 hours at room temperature. To the reaction mixture was added 400 ml of water. The aqueous layer was separated and subjected to re-extraction, which was combined with the extracted organic layer. The resultant organic layer was washed with 400 ml of a saturated aqueous solution of sodium hydrogencarbonate, then with a saturated aqueous saline solution, followed by drying over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to give 121 g (100 %) of (5-ethyl-2-pyridyl)ethyl methanesulfonate as a pale yellow oily product.
Workup
- temperatureunder cooling
- stirringthe mixture was stirred for 3 hours at room temperature
- customThe aqueous layer was separated
- extractionsubjected to re-extraction, which
- washThe resultant organic layer was washed with 400 ml of a saturated aqueous solution of sodium hydrogencarbonate
- dry with materialby drying over anhydrous sodium sulfate
- distillationThe solvent was distilled off under reduced pressure
Sources & evidence
- ORD record
- ord-c23ae05777c7482682742dc587e5c155
- Source dataset
- uspto-grants-1996_09
- Patent number
- US05554758
Reaction notes
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