Acetic Acid → 2-((4-(2-Nitroethyl)benzyl)oxy)pyridine

HRID 78284

반응식

HRID 78284 반응식
[N+:1](/[CH:4]=[CH:5]/[C:6]1[CH:19]=[CH:18][C:9]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[CH:8][CH:7]=1)([O-:3])=[O:2].C(O)(=O)C.[B-].[Na+].O>CS(C)=O.C(OCC)C.C(OCC)(=O)C>[N+:1]([CH2:4][CH2:5][C:6]1[CH:19]=[CH:18][C:9]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[CH:8][CH:7]=1)([O-:3])=[O:2]

참가 물질

8

반응물 4

HCID 176Acetic AcidHCID 962WaterHCID 22959485VertellusHCID 58076258(E)-2-((4-(2-Nitrovinyl)benzyl)oxy)pyridine

생성물 1

HCID 580762662-((4-(2-Nitroethyl)benzyl)oxy)pyridine수율 49%

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매HCID 3283Diethyl Ether용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 2-(4-((E)-2-nitro-vinyl)-benzyloxy)-pyridine described in Manufacturing Example 230-1-3 (30.8 g, 120 mmol) and acetic acid (7.4 mL) in dimethyl sulfoxide (150 mL) was added sodium borohydrate (2.45 g, 64.8 mmol) at 30° C. or below. The reaction solution was stirred for 40 minutes at room temperature. Water, ethyl acetate and diethyl ether were added to the reaction solution at 30° C. or below, which was partitioned into aqueous and organic layers. The aqueous layer was extracted with ethyl acetate. The previously obtained organic layer and the ethyl acetate layer were combined, washed with water (3 times) and aqueous sodium chloride (once), dried over anhydrous magnesium sulfate, and then filtered. The filtrate was concentrated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:4) to obtain the title compound (15.2 g, 49%).

후처리

  1. customwhich was partitioned into aqueous and organic layers
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washwashed with water (3 times) and aqueous sodium chloride (once),
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under a reduced pressure
  7. customThe residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:4)

출처 및 근거

ORD 기록
ord-4629484faaaf4b1fa005f795d681f7d8
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841327B2

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