Reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[C:10]2[CH2:13][CH2:14][OH:15])=[CH:5][CH:4]=1.C(N(CC)CC)C.[S:23](Cl)([CH3:26])(=[O:25])=[O:24].O>ClCCl>[CH3:26][S:23]([O:15][CH2:14][CH2:13][C:10]1[C:11]2[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=2)[CH:7]=[CH:8][CH:9]=1)(=[O:25])=[O:24]Participants
6
Conditions
- Temperature
- 0 °C
Procedure
2-(7-Methoxy-1-naphthyl)ethanol (25 mmol) and triethylamine (30 mmol) are dissolved in 50 ml of dichloromethane and the reaction mixture is cooled to 0° C. using an ice bath. Mesyl chloride (30 mmol) is added dropwise and the reaction mixture is stirred at ambient temperature for 2 hours and then poured into 100 ml of water. The organic phase is washed with 1M hydrochloric acid solution and then with water, dried over magnesium sulphate and evaporated. The oil obtained is precipitated from a mixture of diethyl ether/petroleum ether (1/1). The title product is filtered off under suction and then recrystallised from to diisopropyl ether.
Workup
- washThe organic phase is washed with 1M hydrochloric acid solution
- dry with materialwith water, dried over magnesium sulphate
- customevaporated
- customThe oil obtained
- customis precipitated from a mixture of diethyl ether/petroleum ether (1/1)
- filtrationThe title product is filtered off under suction
- customrecrystallised from to diisopropyl ether
Sources & evidence
- ORD record
- ord-3ed8828f72094897973923c2cbadfc7a
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07947852B2
Linked notes
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