Ethylene Glycol → HCID 86690776, compound

HRID 1471739Notes

Reaction equation

HRID 1471739 reaction equation
[OH:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][C:5]([O:10][CH3:11])=[N:4][CH:3]=1.[CH2:12](O)[CH2:13][OH:14].CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[O:9]1[CH2:12][CH2:13][O:14][CH:8]1[C:7]1[CH:6]=[C:5]([O:10][CH3:11])[N:4]=[CH:3][C:2]=1[OH:1]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 722124985-Hydroxy-2-methoxyisonicotinaldehyde

Product 1

HCID 86690776HCID 86690776, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To 5-hydroxy-2-methoxyisonicotinaldehyde (1.0 g, 6.54 mmol, 1.0 eq.) in toluene (50.0 mL) were added ethane-1,2-diol (10.0 mL) and PTSA (248 mg, 1.31 mmol, 0.2 eq.). The mixture was heated to reflux O/N, cooled to rt, neutralized to pH 8, and extracted with EtOAc three times. The combined organic layers were washed with brine, dried over Na2SO4, and concentrated to give 4-(1,3-dioxolan-2-yl)-6-methoxypyridin-3-ol (980 mg, 76%) as an off-white solid. LRMS (M+H+) m/z 198.1.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux O/N
  3. extractionextracted with EtOAc three times
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a7de29871273412a98a3460ff4611b2b
Source dataset
uspto-grants-2015_04
Patent number
US09012450B2

Reaction notes

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