Ethyl orthoformate → HCID 58079761, compound

HRID 1747540Notes

Reaction equation

HRID 1747540 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5](C=O)=[CH:4][N:3]=1.[CH:10]([O:17][CH2:18][CH3:19])([O:14][CH2:15][CH3:16])OCC>C(O)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:10]([O:14][CH2:15][CH3:16])[O:17][CH2:18][CH3:19])=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 31214Ethyl orthoformateHCID 117692346-Bromo-3-pyridinecarboxaldehyde

Product 1

HCID 58079761HCID 58079761, compoundYield 92.2%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 702EthanolSolvent

Procedure

In ethanol (60 mL) was dissolved 6-bromonicotinaldehyde (2.00 g, 10.8 mmol). Triethyl orthoformate (5.37 mL, 32.3 mmol) and p-toluenesulfonic acid monohydrate (102 mg, 0.538 mmol) were added and the mixture was refluxed for 2 hours. The solvent in the reaction mixture was evaporated under reduced pressure, and a saturated aqueous sodium bicarbonate solution and water were added. Extraction with ethyl acetate, washing with saturated brine and drying over anhydrous sodium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1) to give 2-bromo-5-(diethoxymethyl)pyridine (2.59 g, 92% yield).

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. customThe solvent in the reaction mixture was evaporated under reduced pressure
  3. additiona saturated aqueous sodium bicarbonate solution and water were added
  4. extractionExtraction with ethyl acetate
  5. washwashing with saturated brine
  6. dry with materialdrying over anhydrous sodium sulfate
  7. filtrationAfter filtration
  8. customthe solvent in the filtrate was evaporated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-34323a20311840a787260d0b85cfb50e
Source dataset
uspto-grants-2015_10
Patent number
US09150569B2

Reaction notes

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