Dimethyl Sulfoxide → 4-(4-Pyridyl)benzaldehyde

HRID 1264208노트

반응식

HRID 1264208 반응식
C(Cl)(=O)C(Cl)=O.CS(C)=O.[N:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:24]=[CH:23][C:20]([CH2:21][OH:22])=[CH:19][CH:18]=2)=[CH:13][CH:12]=1.CCN(CC)CC>C(Cl)Cl.C(Cl)Cl.CS(C)=O>[N:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:24]=[CH:23][C:20]([CH:21]=[O:22])=[CH:19][CH:18]=2)=[CH:13][CH:12]=1

참가 물질

7

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 2795556(4-(Pyridin-4-yl)phenyl)methanol

생성물 1

HCID 6396734-(4-Pyridyl)benzaldehyde

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 21912085Dimethylsulfoxide-dichloromethane용매

실험 절차

To a cooled (−78° C.) solution of oxalyl chloride in CH2Cl2 (15 mL, 1M) is added, dropwise, DMSO (3 mL). The resulting solution is stirred for 5 minutes then a solution of 4-[pyridin-4-yl]-benzyl alcohol (2.80 g, 15 mmol) (reference example 13a) in CH2Cl2/DMSO (27 mL, 3:1 CH2Cl2/DMSO) is added dropwise. The resulting mixture is stirred 5 minutes then Et3N added (15 mL, 108 mmol) in one portion. The cold bath is removed and stirring continued for 15 minutes. The reaction mixture is then diluted with ethyl acetate, washed with water and then brine, dried over MgSO4 and concentrated. The crude, orange solid product is used without further purification.

후처리

  1. additionis added
  2. stirringThe resulting mixture is stirred 5 minutes
  3. customThe cold bath is removed
  4. stirringstirring
  5. waitcontinued for 15 minutes
  6. additionThe reaction mixture is then diluted with ethyl acetate
  7. washwashed with water
  8. dry with materialbrine, dried over MgSO4
  9. concentrationconcentrated
  10. customThe crude, orange solid product is used without further purification

출처 및 근거

ORD 기록
ord-addbce00117b4a3a8b2ee9083358a383
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06541505B1

반응 노트

불러오는 중…