Dimethyl Sulfoxide → 5-(3-Pyridinyl)-2-pentanone

HRID 1458364Notes

Reaction equation

HRID 1458364 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][CH:20]([OH:22])[CH3:21])[CH:12]=1.C(N(CC)CC)C>O>[N:11]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][CH2:18][CH2:19][C:20](=[O:22])[CH3:21])[CH:12]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 13739739HCID 13739739, compound

Product 1

HCID 137397405-(3-Pyridinyl)-2-pentanoneYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of oxalyl chloride (0.060 mL in 1 mL dry methylene chloride) at -78° C. was added a solution of methyl sulfoxide (0.075 mL in 0.25 mL methylene chloride) and the mixture stirred at low temperature for 18 minutes. A solution of 5-pyridin-3-yl-pentan-2-ol (71 mg in 1 mL methylene chloride) and the reaction allowed to proceed for 40 minutes after which time 0.35 mL triethylamine were added and the mixture allowed to warm to room temperature. After 35 minutes, water was addded and the mixture extracted with methylene chloride. The organic portion was washed with saturated sodium bicarbonate, dried over sodium sulfate and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (methylene chloride:methanol, 96:4) gave the title compound (61 mg).

Workup

  1. waitto proceed for 40 minutes
  2. waitAfter 35 minutes
  3. extractionthe mixture extracted with methylene chloride
  4. washThe organic portion was washed with saturated sodium bicarbonate
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customPurification of the residue by flash chromatography on silica gel (methylene chloride:methanol, 96:4)

Sources & evidence

ORD record
ord-f6f5ad1e104d45a7995ddefb0711f97d
Source dataset
uspto-grants-1998_12
Patent number
US05849764

Reaction notes

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