Triethylamine → 2-(6-Methylpyridin-2-yl)ethyl methanesulfonate

HRID 60806

Reaction equation

[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][C:7]1[N:12]=[C:11]([CH2:13][CH2:14][OH:15])[CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:1][S:2]([O:15][CH2:14][CH2:13][C:11]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:6])[N:12]=1)(=[O:4])=[O:3]

Participants

Conditions

Temperature: 0 °C

Procedure

MsCl (6.7 mmol, 0.52 mL) was added to a solution of 6-methyl-2-pyridineethanol (6.7 mmol, 0.92 g) and triethyl amine (13.4 mmol, 1.88 mL) in toluene (6 mL) at 0° C. dropwise. The resulting mixture was stirred at 0° C. for 30 min. The precipitate generated from reaction was filtered off. The filtrate was concentrated in vacuo to give crude 2-(6-methylpyridin-2-yl)ethyl methanesulfonate which was used for next step without further purification. A mixture of above described 2-(6-methylpyridin-2-yl)ethyl methanesulfonate, PhOH (13.4 mmol, 1.26 g) and NaOH (13.4 mmol, 0.54 g) in isopropanol (20 mL) was refluxed at 90° C. for 3 h. The reaction mixture was concentrated in vacuo and dissolved in EtOAc which was washed with water. The organic layer was separated, dried with MgSO4 and concentrated in vacuo. The crude product was purified by chromatography to give desired 2-methyl-6-(2-phenoxyethyl)pyridine as a colorless oil in 26% yield.

Workup

customThe precipitate generated from reaction
filtrationwas filtered off
concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-5815eb26c1a244d6995a88f54424a4fe
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440982B2

Linked notes

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