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

HRID 1944431

反応式

HRID 1944431 の反応式
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

参加物

6

反応物 3

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

生成物 1

HCID 866521924-Phenylsulfonylpyridine-3-carbaldehyde収率 158.8%

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-2d2b5b69f1934b8688454f168f93da75
出典データセット
uspto-grants-2013_03
特許番号
US08394836B2

関連ノート

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