Dimethyl Sulfoxide → 4-(4-Pyridyl)benzaldehyde

HRID 1359599Notes

Reaction equation

HRID 1359599 reaction equation
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

Participants

7

Reactant 4

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

Product 1

HCID 6396734-(4-Pyridyl)benzaldehyde

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21912085Dimethylsulfoxide-dichloromethaneSolvent

Procedure

To a cooled (−78° C.) solution of oxalyl chloride in CH2Cl2 (15 mL, 1M) was added, dropwise, DMSO (3 mL). The resulting solution was stirred for 5 min then a solution of 4-[pyridin-4-yl]-benzyl alcohol (2.80 g, 15 mmol) (reference example 19a) in CH2Cl2/DMSO (27 mL, 3:1 CH2Cl2/DMSO) was added dropwise. The resulting mixture was stirred 5 min then Et3N added (15 mL, 108 mmol) in one portion. The cold bath was removed and stirring continued for 15 min. The reaction mixture was then diluted with ethyl acetate, washed with water and then brine, dried over MgSO4 and concentrated. The crude, orange solid product was used without further purification.

Workup

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

Sources & evidence

ORD record
ord-cc942770c0b8462ebdbba967f8193d45
Source dataset
uspto-grants-2003_07
Patent number
US06599918B2

Reaction notes

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