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

HRID 78258노트

반응식

HRID 78258 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-474e9c06bf91482da949cede5fb24f00
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841327B2

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