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

HRID 1600167Notes

Reaction equation

HRID 1600167 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=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>ClCCl.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 53.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-70 °C

Procedure

Dimethylsulphoxide (18.9 ml) in dry dichloromethane (120 ml) was added over20 minutes to a stirred solution of oxalyl chloride (11.55 ml) in dry dichloromethane (225 ml) at -70° C. The mixture was stirred at -70° C. for 10 minutes and then a solution of 3-(3-pyridyl)propanol(16.56 g) in dry dichloromethane (120 ml) was added with stirring over 20 minutes. Stirring was continued at -70° C. for a further 20 minutesand then triethylamine (50.55 ml) was added dropwise and the temperature was allowed to rise to room temperature. Water (200 ml) was added and the layers were separated. The organic layer was washed twice with water, dried (MgSO4) and evaporated. The residue was distilled to give the title compound as an oil (8.80 g), b.p. 88°-92° C. @ 0.3 mm., Rf. 0.15 (SS2). δ(CDCl3): 2.80(3H,t), 2.93(3H,t), 7.18-7.21 (1H,m), 7.50(1H,d), 8.40-8.45(2H,m), 9.80(1H,s).

Workup

  1. stirringwith stirring over 20 minutes
  2. stirringStirring
  3. customwas continued at -70° C. for a further 20
  4. customto rise to room temperature
  5. customthe layers were separated
  6. washThe organic layer was washed twice with water
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. distillationThe residue was distilled

Sources & evidence

ORD record
ord-d1ff5651f20a4e1a889c82a2a05764cc
Source dataset
uspto-grants-1998_04
Patent number
US05744488

Reaction notes

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