Ethyl orthoformate → HCID 58079761, compound

HRID 2178104Notes

Reaction equation

HRID 2178104 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.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[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 3

HCID 31214Ethyl orthoformateHCID 521998p-Toluenesulfonic acid monohydrateHCID 117692346-Bromo-3-pyridinecarboxaldehyde

Product 1

HCID 58079761HCID 58079761, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In ethanol (50 mL) was dissolved 6-bromonicotinaldehyde (6.00 g, 32.3 mmol). Triethyl orthoformate (10.74 mL, 64.5 mmol) and p-toluenesulfonic acid mono-hydrate (307 mg, 1.613 mmol) were added and the mixture was reflexed for 3 hours. The solvent was evaporated from the mixture under reduced pressure. A saturated sodium bicarbonate solution and water were added and extraction with ethyl acetate was performed. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and filtered. The solvent was evaporated from the filtrate under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1) to give compound BC1 (7.60 g, 91% yield).

Workup

  1. customThe solvent was evaporated from the mixture under reduced pressure
  2. additionA saturated sodium bicarbonate solution and water were added
  3. extractionextraction with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customThe solvent was evaporated from the filtrate under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1)
  9. customto give compound BC1 (7.60 g, 91% yield)

Sources & evidence

ORD record
ord-b8ef83a6900c4f7ea63940933b980f3f
Source dataset
uspto-grants-2015_06
Patent number
US09067923B2

Reaction notes

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