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

HRID 1915210Notes

Reaction equation

HRID 1915210 reaction equation
C(OCC)(=O)C.[N:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][CH2:14][CH2:15][OH:16])[CH:8]=1.CS(C)=O>C(N(CC)CC)C>[N:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][CH2:14][CH:15]=[O:16])[CH:8]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 8857Ethyl AcetateHCID 178613-Pyridinepropanol

Product 1

HCID 111054123-(Pyridin-3-yl)propanalYield 67.7%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

To an ethyl acetate (30 mL) solution of 3-(3-pyridyl)propanol (1.5 g) were added dimethyl sulfoxide (15 mL) and triethylamine (9 mL), a pyridine sulfur trioxide complex (5.2 g) was added while the mixture was stirred at 0° C., and the mixture was stirred as it was for 2 hours. The reaction mixture was concentrated under reduced pressure, and purified by silica gel column chromatography (hexane:ethyl acetate=30:70→0:100) to obtain a titled compound (1:1 g) having the following physical property values.

Workup

  1. additiona pyridine sulfur trioxide complex (5.2 g) was added while the mixture
  2. stirringthe mixture was stirred as it
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. custompurified by silica gel column chromatography (hexane:ethyl acetate=30:70→0:100)

Sources & evidence

ORD record
ord-f2ed175d3134429290007567c7dfd427
Source dataset
uspto-grants-2013_12
Patent number
US08614340B2

Reaction notes

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