Ethylene Glycol → HCID 44754838, compound

HRID 1011649Notes

Reaction equation

HRID 1011649 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]=[O:9])=[N:6][CH:7]=1.[CH2:10](O)[CH2:11][OH:12]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[O:12][CH2:11][CH2:10][O:9]2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 174Ethylene GlycolHCID 98775625-Bromopyridine-2-carbaldehyde

Product 1

HCID 44754838HCID 44754838, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 5-bromopyridine-2-aldehyde (3.72 g, 20 mmol) in toluene (60 mL) was added TsOH monohydrate (190 mg, 1 mmol) and ethane-1,2-diol (2.48 g, 40 mmol). The mixture was heated to reflux for 6 hours. The solvent was removed, and the residue was dissolved in ethyl acetate and washed with sodium bicarbonate and brine. The organic layer was dried with sodium sulfate and concentrated to give the crude product. MS: calc'd 230 (MH+), exp 230 (MH+).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 6 hours
  3. customThe solvent was removed
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washwashed with sodium bicarbonate and brine
  6. dry with materialThe organic layer was dried with sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-54ea6b959f4c4879973c7e3f87324514
Source dataset
uspto-grants-2011_07
Patent number
US07977372B2

Reaction notes

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