Acetic Acid → 2-Methyl-6-(4-(2-nitro-ethyl)-benzyloxy)pyridine

HRID 1690913

반응식

HRID 1690913 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13](/[CH:16]=[CH:17]/[N+:18]([O-:20])=[O:19])=[CH:12][CH:11]=2)[N:3]=1.C(O)(=O)C.[BH4-].[Na+].O>CS(C)=O>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][N+:18]([O-:20])=[O:19])=[CH:12][CH:11]=2)[N:3]=1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 592553682-Methyl-6-(4-((E)-2-nitro-vinyl)-benzyloxy)-pyridine

생성물 1

HCID 580762612-Methyl-6-(4-(2-nitro-ethyl)-benzyloxy)pyridine수율 56%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

To a solution of 2-methyl-6-(4-((E)-2-nitro-vinyl)-benzyloxy)-pyridine (5.00 g, 18.5 mmol) described in Manufacturing Example 3-1-3 and acetic acid (5 mL) in dimethyl sulfoxide (50 mL) was added sodium borohydride (1.2 g, 29.6 mmol) under nitrogen atmosphere at room temperature while cooling appropriately, which was stirred for 10 minutes at room temperature. Water was then added dropwise. The mixture was partitioned into water and ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:5 then 1:2) to obtain the title compound (2.8 g, 56%).

후처리

  1. temperaturewhile cooling appropriately
  2. customThe mixture was partitioned into water and ethyl acetate
  3. washThe organic layer was washed with water and saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under a reduced pressure
  6. customThe residue was purified by NH silica gel column chromatography (ethyl acetate

출처 및 근거

ORD 기록
ord-58dff9efca0c46f18789e4378ccceec7
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153662B2

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