Acetic Acid → 1-(2-Nitro-ethyl)-3-phenoxy-benzene

HRID 77965노트

반응식

HRID 77965 반응식
CS(C)=O.[N+:5](/[CH:8]=[CH:9]/[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:11]=1)([O-:7])=[O:6].C(O)(=O)C.[BH4-].[Na+]>O>[N+:5]([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:11]=1)([O-:7])=[O:6]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 679Dimethyl SulfoxideHCID 4311764Sodium borohydrideHCID 57025051-(2-Nitroethenyl)-3-phenoxybenzene

생성물 1

HCID 592551701-(2-Nitro-ethyl)-3-phenoxy-benzene수율 68.1%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a dimethyl sulfoxide (30.0 mL) solution of 1-((E)-2-nitro-vinyl)-3-phenoxy-benzene (3.60 g, 14.9 mmol) described in Manufacturing Example 64-1-1 and acetic acid (3.00 mL) was added sodium borohydride (902 mg, 23.8 mmol) at room temperature while cooling appropriately under nitrogen atmosphere, which was stirred for 3 minutes. Water was then added dropwise at room temperature while cooling appropriately. The reaction mixture was extracted with ethyl acetate, and the organic layer was washed with water and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduce pressure, and the residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:5) to obtain the title compound (2.47 g, 68.1%).

후처리

  1. temperaturewhile cooling appropriately under nitrogen atmosphere
  2. temperaturewhile cooling appropriately
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. washthe organic layer was washed with water and saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under a reduce pressure
  8. customthe residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:5)

출처 및 근거

ORD 기록
ord-1a2d720998ef4415a6434f30c7b3a947
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841327B2

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