Methanol → HCID 18676102, compound

HRID 1635483Notes

Reaction equation

HRID 1635483 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=1)(=[O:4])[CH2:2][CH3:3].COC(OC)N(C)C.[CH3:19][OH:20]>>[N:8]1[CH:9]=[CH:10][C:5]([C:1](=[O:4])[CH:2]([CH3:3])[CH:19]=[O:20])=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 743431-(4-Pyridinyl)-1-propanoneHCID 78373Dimethylformamide dimethyl acetal

Product 1

HCID 18676102HCID 18676102, compoundYield 81%

Procedure

A mixture of 4-propionylpyridine (5 g, 36.99 mmol) and dimethylformamide dimethylacetal(10 mL, 75.28 mmol) was heated to reflux overnight. After cooling to room temperature, methanol generated in situ was removed from reaction mixture under reduced pressure, providing a brown color solid. The crude product was purified by column chromatography (silica gel, 3:7 EtOAc/haxane) to give the named compound (5.73 g, 81%) as a brown oil.

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customwas removed from reaction mixture under reduced pressure
  4. customproviding a brown color solid
  5. customThe crude product was purified by column chromatography (silica gel, 3:7 EtOAc/haxane)

Sources & evidence

ORD record
ord-43890e9440754d12b2a28537d112ca44
Source dataset
uspto-grants-2003_01
Patent number
US06509361B1

Reaction notes

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