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Cesium carbonate → Diethyl 2,2'-((5-(1-(((4-(trifluoromethyl)benzyl)oxy)imino)ethyl)oxazol-2-yl)azanediyl)diacetate

HRID 68320
ノート
印刷プレビュー

反応式

HRID 68320 の反応式
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[OH:19][N:20]=[C:21]([C:23]1[O:27][C:26]([N:28]([CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[N:25][CH:24]=1)[CH3:22]>CN(C=O)C>[F:10][C:9]([F:12])([F:11])[C:6]1[CH:7]=[CH:8][C:3]([CH2:2][O:19][N:20]=[C:21]([C:23]2[O:27][C:26]([N:28]([CH2:35][C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[N:25][CH:24]=2)[CH3:22])=[CH:4][CH:5]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 86699627Diethyl 2,2'-((5-(1-(hydroxyimino)ethyl)oxazol-2-yl)azanediyl)diacetate

生成物 1

HCID 86699628Diethyl 2,2'-((5-(1-(((4-(trifluoromethyl)benzyl)oxy)imino)ethyl)oxazol-2-yl)azanediyl)diacetate収率 75%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

実験手順

To a solution of 1-(bromomethyl)-4-(trifluoromethyl)benzene (200 mg, 0.84 mmoles) in DMF (2 mL), cesium carbonate (408 mg, 1.26 mmoles) was added followed by addition of diethyl 2,2′-((5-(1-(hydroxyimino)ethyl)oxazol-2-yl)azanediyl)diacetate (262 mg, 0.84 mmoles) at 25° C. under nitrogen atmosphere and the reaction mixture was stirred at the same temperature for 18 h. The reaction mixture was poured into ice cold water and extracted with ethyl acetate. The combined ethyl acetate extract was washed with water & brine, dried over sodium sulphate and evaporated under reduced pressure. The crude product was purified by column chromatography (Eluent: 15% ethyl acetate in hexane) to yield 295 mg (75%) product as thick liquid.

後処理

  1. additionThe reaction mixture was poured into ice cold water
  2. extractionextracted with ethyl acetate
  3. extractionThe combined ethyl acetate extract
  4. washwas washed with water & brine
  5. dry with materialdried over sodium sulphate
  6. customevaporated under reduced pressure
  7. customThe crude product was purified by column chromatography (Eluent: 15% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-af5626932dec4aa0816055572b30561f
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08822414B2

反応ノート

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