Water → 2-(6-Chloro-2-methoxypyridin-3-yl)ethan-1-ol

HRID 233729

반응식

HRID 233729 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[N:3]=1.[Li]CCCC.[CH2:15]1[O:17][CH2:16]1.O>C1COCC1.CCOCC>[OH:17][CH2:16][CH2:15][C:5]1[C:4]([O:8][CH3:9])=[N:3][C:2]([Cl:1])=[CH:7][CH:6]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 6354Ethylene OxideHCID 870092-Chloro-6-methoxypyridineHCID 178418339Butyllithium

생성물 1

HCID 197036802-(6-Chloro-2-methoxypyridin-3-yl)ethan-1-ol

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 1.0 g (7.0 mmol) of 2-chloro-6-methoxypyridine in 20 ml of dry THF cooled to -78° C. was added 10.9 ml (1.6M in hexanes, 17.4 mmol) n-BuLi under an atmosphere of nitrogen. The temperature of the mixture was allowed to raise to -40° C. before an addition of 4 ml ethylene oxide in 6 ml ether. The mixture was warmed to room temperature, 50 ml water was added and the aqueous layer was separated and extracted with 2×100 ml EtOAc. The organic extracts were combined, washed once with water, dried with Na2SO4, and concentrated in vacuo. The crude material was purified by dry column flash chromatography (hexane/EtOAc) to afford 0.22 g of 3-(2-hydroxyethyl)-6-chloro-2-methoxypyridine as a yellowish oil.

후처리

  1. customthe aqueous layer was separated
  2. extractionextracted with 2×100 ml EtOAc
  3. washwashed once with water
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified
  7. dry with materialby dry column flash chromatography (hexane/EtOAc)

출처 및 근거

ORD 기록
ord-825c65e13c79422983a8fc57b77d283f
출처 데이터셋
uspto-grants-1997_01
특허 번호
US05593993

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