Ethylene Glycol → HCID 44754838, compound

HRID 2420653Notes

Reaction equation

HRID 2420653 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].C1(C)C=CC(S(O)(=O)=O)=CC=1.[Br:16][C:17]1[CH:18]=[CH:19][C:20]([CH:23]=O)=[N:21][CH:22]=1>C1(C)C=CC=CC=1>[Br:16][C:17]1[CH:18]=[CH:19][C:20]([CH:23]2[O:4][CH2:1][CH2:2][O:3]2)=[N:21][CH:22]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 98775625-Bromopyridine-2-carbaldehyde

Product 1

HCID 44754838HCID 44754838, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Ethyleneglycol (14.88 g, 0.24 mol) and p-toluenesulfonic acid (3 g, 0.16 mol) are added to a solution of 5-bromopyridine-2-carbaldehyde (30 g, 0.16 mol) in toluene (150 ml) at room temperature and the mixture is stirred for 10 hrs at refluxing temperature. After cooling to room temperature, the mixture is quenched with saturated aqueous NH4Cl, extracted with CH2Cl2 and washed with H2O. The aqueous layer is extracted with CH2Cl2 and the combined organic extract is washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (hexane-AcOEt (9:1 V/V)) to afford 5-bromo-2-(1,3-dioxolan-2-yl)pyridine (30.9 g, 84%) as a colorless oil. %). 1H NMR (400 MHz, CDCl3) δ 8.69 (s, 1H), 7.87 (m, 1H), 7.45 (m, 1H), 5.83 (s, 1H), 4.13 (m, 4H).

Workup

  1. temperatureat refluxing temperature
  2. customthe mixture is quenched with saturated aqueous NH4Cl
  3. extractionextracted with CH2Cl2
  4. washwashed with H2O
  5. extractionThe aqueous layer is extracted with CH2Cl2
  6. extractionthe combined organic extract
  7. washis washed with brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated under reduced pressure
  10. customThe residue is purified by silica gel column chromatography (hexane-AcOEt (9:1 V/V))

Sources & evidence

ORD record
ord-f1d94a70a38a45f89e8192cf40767d5b
Source dataset
uspto-grants-2011_06
Patent number
US07955720B2

Reaction notes

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