Acetone → 2-(6-Bromo-5-methoxypyridin-2-yl)propan-2-ol

HRID 604225

반응식

HRID 604225 반응식
[Br:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4](I)[N:3]=1.C([Li])CCC.[CH3:16][C:17]([CH3:19])=[O:18].O>C1(C)C=CC=CC=1.CCCCCC.C(OCC)(=O)C>[Br:1][C:2]1[N:3]=[C:4]([C:17]([OH:18])([CH3:19])[CH3:16])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

참가 물질

8

반응물 4

HCID 180AcetoneHCID 962WaterHCID 110990402-Bromo-6-iodo-3-methoxypyridineHCID 178418339Butyllithium

생성물 1

HCID 575560732-(6-Bromo-5-methoxypyridin-2-yl)propan-2-ol

시약·촉매·용매 3

HCID 1140Toluene용매HCID 8058Hexane용매HCID 8857Ethyl Acetate용매

실험 절차

2-Bromo-6-iodo-3-methoxy-pyridine (500 mg) is dissolved in dry toluene (5 ml) and thereto is added dropwise 1.6M n-butyllithium in hexane (1 ml) at −78° C. under nitrogen atmosphere, and the mixture is stirred for 1 hour and thereto is added acetone (0.23 ml), and the mixture is stirred overnight. To the reaction solution are added water and ethyl acetate, and the mixture is separated, and the organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=4:1→3:2) to give 2-(6-bromo-5-methoxy-pyridin-2-yl)-propan-2-ol (197 mg). MS (m/z): 246/248 [M+H]+

후처리

  1. stirringthe mixture is stirred overnight
  2. customthe mixture is separated
  3. washthe organic layer is washed with a saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=4:1→3:2)

출처 및 근거

ORD 기록
ord-35509863473d45fe99c21d5771979cff
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07906517B2

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