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Cesium carbonate → Tert-butyl (4-methoxybutyl)(3-methoxy-2-nitrophenyl)carbamate

HRID 1509462
ノート
印刷プレビュー

反応式

HRID 1509462 の反応式
[CH3:1][O:2][C:3]1[C:4]([N+:17]([O-:19])=[O:18])=[C:5]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:6]=[CH:7][CH:8]=1.CS(O[CH2:25][CH2:26][CH2:27][CH2:28][O:29][CH3:30])(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[CH3:30][O:29][CH2:28][CH2:27][CH2:26][CH2:25][N:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[C:4]=1[N+:17]([O-:19])=[O:18])[C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:13])[CH3:14]
参加物反応条件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 10587951Tert-butyl (3-methoxy-2-nitrophenyl)carbamateHCID 116870064-Methoxybutyl methanesulfonate

生成物 1

HCID 58355557Tert-butyl (4-methoxybutyl)(3-methoxy-2-nitrophenyl)carbamate収率 53.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
65 °C

実験手順

tert-Butyl (3-methoxy-2-nitrophenyl)carbamate (3.00 g) and 4-methoxybutyl methanesulfonate (3.06 g) were dissolved in dimethylformamide (40 ml), cesium carbonate (7.30 g) was added, and the mixture was stirred at 65° C. for 4 hr. The reaction mixture was concentrated under reduced pressure, diluted with water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, and a fraction eluted with ethyl acetate-hexane (5:95-7:3) was concentrated under reduced pressure to give the object product (2.11 g).

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiondiluted with water
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. washa fraction eluted with ethyl acetate-hexane (5:95-7:3)
  8. concentrationwas concentrated under reduced pressure

出典と根拠

ORDレコード
ord-f32ca1fe2e1241e8b7d9b7f5d03a02a8
出典データセット
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09221836B2

反応ノート

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