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

HRID 1843970

반응식

HRID 1843970 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

HCID 207151453-Bromo-4-(dimethoxymethyl)pyridine수율 96.3%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8058Hexane용매

반응 조건

온도
75 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-94b7ec8671794e2c90f43b79de571854
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946260B2

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