Triethylamine → 2-(5-Ethylpyridin-2-yl)ethyl methanesulfonate
Reaction equation
[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][OH:11])=[N:7][CH:8]=1)[CH3:2].C(N(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>C1(C)C=CC=CC=1>[CH3:19][S:20]([O:11][CH2:10][CH2:9][C:6]1[CH:5]=[CH:4][C:3]([CH2:1][CH3:2])=[CH:8][N:7]=1)(=[O:22])=[O:21]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
66.0 g (436 mmol) of 2-(5-ethylpyridin-2-yl)ethanol was dissolved in 500 mL of toluene. 72.5 mL (523 mmol) of triethylamine was added to this solution, at room temperature. The resulting solution was cooled between 0 and 10° C., after which 34.0 mL (438 mmol) of methanesulphonyl chloride was added dropwise during 75 minutes. When addition was completed, it was stirred for 1 hour at room temperature. Next, the organic phase was washed with a saturated solution of sodium bicarbonate (400 mL) and with water (400 mL), and was dried over sodium sulphate, obtaining a toluene solution of 2-(5-ethylpyridin-2-yl)ethyl methanesulphonate, a compound of formula (III) in which Z=OMs.
Workup
- temperatureThe resulting solution was cooled between 0 and 10° C.
- additionWhen addition
- washNext, the organic phase was washed with a saturated solution of sodium bicarbonate (400 mL) and with water (400 mL)
- dry with materialwas dried over sodium sulphate
Sources & evidence
- ORD record
- ord-f0f87e2231f54f18ae3ad7d1b5013fc4
- Source dataset
- uspto-grants-2008_05
- Patent number
- US07375231B2
Reaction notes
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