Dimethyl Sulfoxide → 3-(Pyridin-3-yl)propanal

HRID 1463366Notes

Reaction equation

HRID 1463366 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[N:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][CH2:18][CH2:19][OH:20])[CH:12]=1.C(N(CC)CC)C>C(Cl)Cl.O>[N:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][CH2:18][CH:19]=[O:20])[CH:12]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 178613-PyridinepropanolHCID 65578Oxalyl chloride

Product 1

HCID 111054123-(Pyridin-3-yl)propanalYield 429.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of oxalyl chloride (2.55 g, 20.1 mmol) in anhydrous DCM (150 ml) was cooled to -78° C. and dimethylsulphoxide (3.77g, 40.1 mmol) added dropwise with stirring. After two minutes, 3(3-pyridyl)-1-propanol (0.625 g, 3.79 mmol) was added and stirring continued for a further fifteen minutes Triethylamine (12.70 ml, 91.2 mmol) was then added and stirring continued for five minutes before allowing the solution to warm to room temperature. Water (150 ml) was added the organic layer separated and the aqueous layer extracted with DCM (2×100 ml). The organic extracts were combined, washed with brine (50 ml), dried over anhydrous magnesium sulphate, filtered and evaporated to give a yellow oil (2.20 g, 90%) which was used directly in the next step.

Workup

  1. stirringstirring
  2. waitcontinued for a further fifteen minutes
  3. stirringstirring
  4. waitcontinued for five minutes
  5. customseparated
  6. extractionthe aqueous layer extracted with DCM (2×100 ml)
  7. washwashed with brine (50 ml)
  8. dry with materialdried over anhydrous magnesium sulphate
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-9fe436e6f0c04e6f84c20c195aa2144a
Source dataset
uspto-grants-1994_04
Patent number
US05300524

Reaction notes

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