Dimethyl Sulfoxide → 3-(6-Methyl-2-pyridyl)propanal

HRID 618627

Reaction equation

HRID 618627 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH3:11][C:12]1[N:17]=[C:16]([CH2:18][CH2:19][CH2:20][OH:21])[CH:15]=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl>[CH3:11][C:12]1[N:17]=[C:16]([CH2:18][CH2:19][CH:20]=[O:21])[CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 1091326-Methyl-2-pyridylpropan-1-ol

Product 1

HCID 218475033-(6-Methyl-2-pyridyl)propanalYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-78 °C

Procedure

A solution of DMSO (1.78 g, 22.9 mmol) in dichloromethane (4mL) was added dropwise over 3 min into solution of oxalyl chloride (11.3 mmol) in dichloromethane (6 mL) cooled to -78° C. under nitrogen. The reaction mixture was stirred for 5 min when 3-(6-methyl-2-pyridyl)propanol (1.57 g, 10.4 mmol) in dichloromethane (20 mL) was added over 5 min. The stirring continued for 20 min at -78° C. and triethylamine (8 ml) was added resulting in dark slurry. The cooling bath was removed and after 3 hr, the reaction mixture was quenched with brine followed by dichloromethane extraction (3×). After solvent removal, the dark residue was purified by column chromatography (silica gel, ethyl acetate) yielding a yellow oil (77%). MS (DCI) (M+H)+ at m/z 150.

Workup

  1. additionwas added over 5 min
  2. customresulting in dark slurry
  3. customThe cooling bath was removed and after 3 hr
  4. customthe reaction mixture was quenched with brine
  5. extractionfollowed by dichloromethane extraction (3×)
  6. customAfter solvent removal
  7. customthe dark residue was purified by column chromatography (silica gel, ethyl acetate)

Sources & evidence

ORD record
ord-0ed2cbfb4f644190b758279bd5a09ca1
Source dataset
uspto-grants-1999_09
Patent number
US05955440

Linked notes

Loading…