Cesium carbonate → 2-(2-Iodo-6-methylpyridin-3-yloxy)ethanol

HRID 1913431ノート

反応式

HRID 1913431 の反応式
[I:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:17][CH2:18][OH:19]>CN(C=O)C>[I:1][C:2]1[C:7]([O:8][CH2:17][CH2:18][OH:19])=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=1

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 108982-BromoethanolHCID 899572-Iodo-6-methylpyridin-3-ol

生成物 1

HCID 218737982-(2-Iodo-6-methylpyridin-3-yloxy)ethanol収率 100.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

To a stirred mixture of 2-iodo-6-methylpyridin-3-ol (530 g, 2.25 mol), Cs2CO3 (876 g, 2.7 mol) and DMF (2.5 L) was added 2-bromo-ethanol (560 g, 4.51 mol) dropwise at 0° C. The mixture was stirred at 90° C. overnight. The reaction was cooled and the solvent was removed in vacuo. The residue was diluted with water (2 L) and the aqueous solution was extracted with CH2Cl2 (3×350 mL). The combined organic layers were washed with brine (2×150 mL), dried over anhydrous Na2SO4 and concentrated to afford 2-(2-iodo-6-methylpyridin-3-yloxy)ethanol (630 g) as a brown solid which was used directly in the next step without further purification.

後処理

  1. temperatureThe reaction was cooled
  2. customthe solvent was removed in vacuo
  3. additionThe residue was diluted with water (2 L)
  4. extractionthe aqueous solution was extracted with CH2Cl2 (3×350 mL)
  5. washThe combined organic layers were washed with brine (2×150 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-8afbd1aca60b483abc8ac90904fff18f
出典データセット
uspto-grants-2013_12
特許番号
US08609680B2

反応ノート

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