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

HRID 60806

반응식

HRID 60806 반응식
[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]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 702836-Methylpyridine-2-ethanol

생성물 1

HCID 878851582-(6-Methylpyridin-2-yl)ethyl methanesulfonate

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  1. customThe precipitate generated from reaction
  2. filtrationwas filtered off
  3. concentrationThe filtrate was concentrated in vacuo

출처 및 근거

ORD 기록
ord-5815eb26c1a244d6995a88f54424a4fe
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440982B2

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