Acetic Acid → 3-(4-(2-Nitro-ethyl)-phenoxy)-pyridine

HRID 1691120노트

반응식

HRID 1691120 반응식
CS(C)=O.[N+:5](/[CH:8]=[CH:9]/[C:10]1[CH:22]=[CH:21][C:13]([O:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[CH:12][CH:11]=1)([O-:7])=[O:6].C(O)(=O)C.[BH4-].[Na+]>O>[N+:5]([CH2:8][CH2:9][C:10]1[CH:22]=[CH:21][C:13]([O:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[CH:12][CH:11]=1)([O-:7])=[O:6]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 679Dimethyl SulfoxideHCID 4311764Sodium borohydrideHCID 59255233HCID 59255233, 화합물

생성물 1

HCID 592552763-(4-(2-Nitro-ethyl)-phenoxy)-pyridine수율 40.6%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a dimethyl sulfoxide (15.0 mL) solution of 3-(4-((E)-2-nitro-vinyl)-phenoxy)pyridine (2.00 g, 8.26 mmol) described in Manufacturing Example 76-1-2 and acetic acid (2.00 mL) was added sodium borohydride (500 mg, 13.2 mmol) at room temperature while cooling appropriately under nitrogen atmosphere, which was stirred for 30 minutes at room temperature. 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 reduced pressure, and the residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:3→1:2) to obtain the title compound (819 mg, 40.6%).

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 reduced pressure
  8. customthe residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:3→1:2)

출처 및 근거

ORD 기록
ord-e7580d3cbc794d37943a3cf09d6b4038
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153662B2

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