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

HRID 573530

Reaction equation

HRID 573530 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), dimethyl sulfoxide (15 mL) and triethylamine (9 mL) were added. Additionally, a pyridine sulfur trioxide complex (5.2 g) was added with stirring at 0° C. for 2 hours as it was. 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. additionAdditionally, a pyridine sulfur trioxide complex (5.2 g) was added
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. custompurified by silica gel column chromatography (hexane:ethyl acetate=30:70→0:100)

Sources & evidence

ORD record
ord-75504ef87702452d982eea88f4787d85
Source dataset
uspto-grants-2015_05
Patent number
US09029574B2

Linked notes

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