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

HRID 1913431노트

반응식

HRID 1913431 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
90 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8afbd1aca60b483abc8ac90904fff18f
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08609680B2

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