Triethylamine → 2-(7-Methoxynaphthalen-1-yl)ethyl methanesulfonate
Reaction equation
C(N(CC)CC)C.[S:8](Cl)([CH3:11])(=[O:10])=[O:9].[CH3:13][O:14][C:15]1[CH:24]=[C:23]2[C:18]([CH:19]=[CH:20][CH:21]=[C:22]2[CH2:25][CH2:26][OH:27])=[CH:17][CH:16]=1>ClCCl>[S:8]([O:27][CH2:26][CH2:25][C:22]1[C:23]2[C:18](=[CH:17][CH:16]=[C:15]([O:14][CH3:13])[CH:24]=2)[CH:19]=[CH:20][CH:21]=1)(=[O:10])(=[O:9])[CH3:11]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -10 °C
Procedure
In a 250-cm3 flask, 4 g of 2-(7-methoxy-1-naphthyl)ethanol are dissolved in 100 cm3 of dichloromethane, and 3.3 cm3 of triethylamine are added. The mixture is cooled in an ice bath at -10° C. and 2.75 g of mesyl chloride are then added dropwise and with stirring. The mixture is left stirring for 30 minutes. The aqueous phase is extracted with 3 times 50 cm3 of dichloromethane, and the organic phase is washed with 3 times 20 cm3 of 1N hydrochloric acid solution and then with water, dried over potassium carbonate and evaporated. The oily residue is recrystallized.
Workup
- waitThe mixture is left
- stirringstirring for 30 minutes
- extractionThe aqueous phase is extracted with 3 times 50 cm3 of dichloromethane
- washthe organic phase is washed with 3 times 20 cm3 of 1N hydrochloric acid solution
- dry with materialwith water, dried over potassium carbonate
- customevaporated
- customThe oily residue is recrystallized
Sources & evidence
- ORD record
- ord-930d75a478a44c1f993455a3cf0bd573
- Source dataset
- uspto-grants-1998_03
- Patent number
- US05731352
Reaction notes
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