Sodium hydride → 6-Methyl-2,3-dihydro-[1,4]dioxino[2,3-b]pyridine

HRID 1913432노트

반응식

HRID 1913432 반응식
I[C:2]1[C:7]([O:8][CH2:9][CH2:10][OH:11])=[CH:6][CH:5]=[C:4]([CH3:12])[N:3]=1.[H-].[Na+]>CN(C=O)C.[O-]S([O-])(=O)=O.[Cu+2]>[CH3:12][C:4]1[N:3]=[C:2]2[O:11][CH2:10][CH2:9][O:8][C:7]2=[CH:6][CH:5]=1

참가 물질

5

반응물 2

HCID 24758Sodium hydrideHCID 218737982-(2-Iodo-6-methylpyridin-3-yloxy)ethanol

생성물 1

HCID 156332996-Methyl-2,3-dihydro-[1,4]dioxino[2,3-b]pyridine수율 16%

시약·촉매·용매 2

HCID 24462Copper Sulfate촉매HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

To a stirred solution of 2-(2-iodo-6-methylpyridin-3-yloxy)ethanol (350 g, 1.25 mol) in anhydrous DMF (3.5 L) was added NaH (60 g, 1.5 mol), Cu (33.7 g, 0.53 mol) and CuSO4 (100 g, 0.63 mol) at 0° C. After the addition, the mixture was stirred at 100° C. overnight. After cooling, the solvent was removed in vacuo and the residue was diluted with water (1.5 L). The aqueous solution was extracted with CH2Cl2 (3×350 mL). The combined organic layers were washed with brine (2×100 mL), dried over anhydrous Na2SO4 and concentrated. The residue was purified via column chromatography (silica gel, EtOAc/petroleum ether 1:20) to yield 6-methyl-2,3-dihydro-[1,4]dioxino[2,3-b]pyridine (30.0 g, 16%) as a yellow oil.

후처리

  1. additionAfter the addition
  2. temperatureAfter cooling
  3. customthe solvent was removed in vacuo
  4. additionthe residue was diluted with water (1.5 L)
  5. extractionThe aqueous solution was extracted with CH2Cl2 (3×350 mL)
  6. washThe combined organic layers were washed with brine (2×100 mL)
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated
  9. customThe residue was purified via column chromatography (silica gel, EtOAc/petroleum ether 1:20)

출처 및 근거

ORD 기록
ord-0bcda9c1a9c4405ba511c9d962c19165
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08609680B2

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