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

HRID 1855678Notes

Reaction equation

HRID 1855678 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-a2e17ff38d00409bb85cb54a19a42f1d
Source dataset
uspto-grants-2015_02
Patent number
US08962868B2

Reaction notes

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