Potassium Carbonate → Tert-butyl 2-[(2,5-dichloropyridin-3-yl)oxy]-2-methylpropionate

HRID 1026538ノート

反応式

HRID 1026538 の反応式
[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([Cl:9])=[CH:4][N:3]=1.Br[C:11]([CH3:20])([CH3:19])[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:1][C:2]1[C:7]([O:8][C:11]([CH3:20])([CH3:19])[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[CH:6][C:5]([Cl:9])=[CH:4][N:3]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 90290tert-Butyl 2-bromo-2-methylpropionateHCID 98989172,5-Dichloropyridin-3-Ol

生成物 1

HCID 86671386Tert-butyl 2-[(2,5-dichloropyridin-3-yl)oxy]-2-methylpropionate収率 83.3%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To an acetonitrile solution (400 ml) of 2,5-dichloropyridin-3-ol (20.0 g) (Synthesis, 1990, 6, 499-501) and tert-butyl 2-bromo-2-methylpropionate (54.4 g) was added at room temperature potassium carbonate (30.3 g), followed by stirring for 12 hours under heating at reflux. The insolubles were filtered off, and washed with ethyl acetate. The filtrate was concentrated under reduced pressure, and then the residue was purified by silica gel chromatography to afford tert-butyl 2-[(2,5-dichloropyridin-3-yl)oxy]-2-methylpropionate (31.1 g).

後処理

  1. temperatureunder heating
  2. temperatureat reflux
  3. filtrationThe insolubles were filtered off
  4. washwashed with ethyl acetate
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-2b109e8f43004f1cb6609859453c698d
出典データセット
uspto-grants-2014_05
特許番号
US08729095B2

反応ノート

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