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

HRID 78284

反応式

HRID 78284 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒HCID 3283Diethyl Ether溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-4629484faaaf4b1fa005f795d681f7d8
出典データセット
uspto-grants-2014_09
特許番号
US08841327B2

関連ノート

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