p-Toluenesulfonic acid → 3-Bromo-4-(dimethoxymethyl)pyridine

HRID 1843970

反応式

HRID 1843970 の反応式
[C:1]1(C)C=CC(S(O)(=O)=O)=CC=1.[Br:12][C:13]1[CH:20]=[N:19][CH:18]=[CH:17][C:14]=1[CH:15]=[O:16].[C:21](OCC)(=[O:23])C>CO.CCCCCC>[Br:12][C:13]1[CH:20]=[N:19][CH:18]=[CH:17][C:14]=1[CH:15]([O:23][CH3:21])[O:16][CH3:1]

参加物

6

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 8857Ethyl AcetateHCID 27629973-Bromopyridine-4-carboxaldehyde

生成物 1

HCID 207151453-Bromo-4-(dimethoxymethyl)pyridine収率 96.3%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8058Hexane溶媒

反応条件

温度
75 °C

実験手順

p-Toluene sulphonic acid (PTSA) (613.5 mg, 3.225 mmol) was added to a stirred solution of 3-bromoisonicotinaldehyde (500 mg, 2.688 mmol) in methanol (20 mL) and the resulting reaction mixture was stirred for 3 hours at 75° C. The reaction was monitored by TLC (10% ethyl acetate in hexane). The reaction mixture was cooled to room temperature and concentrated under reduced pressure. The crude residue was diluted with ice, basified using saturated NaHCO3 solution and extracted using ethyl acetate. The organic layer was washed with water, brine solution, dried over Na2SO4 and concentrated under reduced pressure. Purification by column chromatography on silica gel (10% ethyl acetate in hexane) afforded 600 mg of the product (96.3% yield).

後処理

  1. customthe resulting reaction mixture
  2. temperatureThe reaction mixture was cooled to room temperature
  3. concentrationconcentrated under reduced pressure
  4. additionThe crude residue was diluted with ice
  5. extractionextracted
  6. washThe organic layer was washed with water, brine solution
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated under reduced pressure
  9. customPurification by column chromatography on silica gel (10% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-94b7ec8671794e2c90f43b79de571854
出典データセット
uspto-grants-2015_02
特許番号
US08946260B2

関連ノート

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