Acetic Acid → 2-Benzyl-5-(2-nitro-ethyl)-pyridine

HRID 78258ノート

反応式

HRID 78258 の反応式
[CH2:1]([C:8]1[CH:13]=[CH:12][C:11](/[CH:14]=[CH:15]/[N+:16]([O-:18])=[O:17])=[CH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.[BH4-].[Na+]>CS(C)=O>[CH2:1]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][N+:16]([O-:18])=[O:17])=[CH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 592553902-Benzyl-5-((E)-2-nitro-vinyl)-pyridine

生成物 1

HCID 592551352-Benzyl-5-(2-nitro-ethyl)-pyridine収率 22%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

To a mixture of 2-benzyl-5-((E)-2-nitro-vinyl)-pyridine (1.2 g, 5.0 mmol) described in Manufacturing Example 210-1-5, acetic acid (300 mg, 5.0 mmol), and dimethyl sulfoxide (10 mL) was added sodium borohydride (94 mg, 2.5 mmol), which was stirred for 10 minutes at room temperature. The reaction solution was partitioned into ethyl acetate and water. The organic layer was separated and passed through a glass filter provided with NH silica gel (eluted with ethyl acetate). The eluate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (heptane:ethyl acetate=2:1) to obtain the title compound (260 mg, 22%).

後処理

  1. customThe reaction solution was partitioned into ethyl acetate and water
  2. customThe organic layer was separated
  3. filtrationfilter
  4. customprovided with NH silica gel (eluted with ethyl acetate)
  5. concentrationThe eluate was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (heptane:ethyl acetate=2:1)

出典と根拠

ORDレコード
ord-474e9c06bf91482da949cede5fb24f00
出典データセット
uspto-grants-2014_09
特許番号
US08841327B2

反応ノート

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