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

HRID 1913432ノート

反応式

HRID 1913432 の反応式
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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 24462Copper Sulfate触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-0bcda9c1a9c4405ba511c9d962c19165
出典データセット
uspto-grants-2013_12
特許番号
US08609680B2

反応ノート

読み込み中…