N-methyl-2-pyrrolidone → 4-Phenylsulfonylpyridine-3-carbaldehyde

HRID 1944431

반응식

HRID 1944431 반응식
Br[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[CH:8]=[O:9].[Na+].[C:11]1([S:17]([O-:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.CN1CCCC1=O>C(OCC)(=O)C.[Cu]I>[C:11]1([S:17]([C:2]2[CH:7]=[CH:6][N:5]=[CH:4][C:3]=2[CH:8]=[O:9])(=[O:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

참가 물질

6

반응물 3

HCID 13387N-methyl-2-pyrrolidoneHCID 2723840Benzenesulfinic acid, sodium saltHCID 111167404-Bromopyridine-3-carbaldehyde

생성물 1

HCID 866521924-Phenylsulfonylpyridine-3-carbaldehyde수율 158.8%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 8857Ethyl Acetate용매

반응 조건

온도
60 °C

실험 절차

A mixture of 4-bromopyridine-3-carbaldehyde (0.90 g), benzenesulfinic acid sodium salt (4.0 g), copper (I) iodide (4.6 g) and 1-methyl-2-pyrrolidinone (50 mL) was heated at 60° C. for 2 hours. The mixture was cooled to room temperature, diluted with ethyl acetate and filtered through Celite. The filtrate was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with a mixture of cyclohexane and ethyl acetate (1:0 to 0:1 by volume) to afford the title compound as a yellow oil (1.9 g).

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered through Celite
  3. washThe filtrate was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel
  7. washeluting with a mixture of cyclohexane and ethyl acetate (1:0 to 0:1 by volume)

출처 및 근거

ORD 기록
ord-2d2b5b69f1934b8688454f168f93da75
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394836B2

연결된 노트

불러오는 중…