Triphenylphosphine → 6-bromo-4-methylene-3,4-dihydro-2H-pyrano[3,2-b]pyridine

HRID 1478547

反応式

HRID 1478547 の反応式
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC([O-])=O.[K+].Br[C:26]1[C:31]([O:32][CH2:33][CH2:34][CH:35]=[CH2:36])=[CH:30][CH:29]=[C:28]([Br:37])[N:27]=1>[N+](CC)(CC)(CC)CC.[Cl-].CN(C=O)C.CCOC(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[Br:37][C:28]1[N:27]=[C:26]2[C:35](=[CH2:36])[CH2:34][CH2:33][O:32][C:31]2=[CH:30][CH:29]=1

参加物

8

反応物 3

HCID 11776TriphenylphosphineHCID 517044Potassium AcetateHCID 584840892,6-Dibromo-3-(but-3-enyloxy)pyridine

生成物 1

HCID 584840716-bromo-4-methylene-3,4-dihydro-2H-pyrano[3,2-b]pyridine

試薬・触媒・溶媒 4

HCID 5946Tetraethylammonium Chloride触媒HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
105 °C

実験手順

To a stirred mixture of PPh3(67.6 g, 0.258 mol), KOAc (42 g, 0.43 mol), Pd(OAc)2 (1.94 g, 8.6 mmol) and Et4NCl (28.6 g, 0.172 mmol), was added 2,6-dibromo-3-(but-3-enyloxy) pyridine (26.4 g, 0.086 mol) in anhydrous DMF (300 ml). The mixture was heated at 105° C. overnight. After cooling to rt, the mixture was dissolved in EtOAc, washed with water and brine, dried over Na2SO4, and concentrated in vacuo. The crude product was purified by silica gel chromatography (petroleum) to afford the title compound as an oil.

後処理

  1. temperatureAfter cooling to rt
  2. washwashed with water and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by silica gel chromatography (petroleum)

出典と根拠

ORDレコード
ord-74758aa85cad44d1b52f3869b620be18
出典データセット
uspto-grants-2016_08
特許番号
US09403845B2

関連ノート

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