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

HRID 77807

反応式

HRID 77807 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-fb5f696084754aee9b49fa86364b773a
出典データセット
uspto-grants-2014_09
特許番号
US08841327B2

関連ノート

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