Benzyl Bromide → HCID 58368201, compound

HRID 2365261Notes

Reaction equation

HRID 2365261 reaction equation
[O:1]=[C:2]1[NH:7][CH:6]=[C:5]([C:8]([O:10][CH3:11])=[O:9])[CH:4]=[CH:3]1.[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Al]>C1C=CC=CC=1.C(OCC)(=O)C.C(=O)([O-])[O-].[Ag+2]>[CH2:12]([O:1][C:2]1[N:7]=[CH:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][CH:3]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 3

HCID 7498Benzyl BromideHCID 416343Methyl 6-oxo-1,6-dihydropyridine-3-carboxylateHCID 5359268Aluminum

Product 1

HCID 58368201HCID 58368201, compound

Reagents, catalysts & solvents 3

HCID 178418647HCID 178418647, compoundCatalystHCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 6-oxo-1,6-dihydropyridine-3-carboxylate (2.00 g, 13.1 mmol) in 45 mL of benzene was added benzyl bromide (1.86 mL, 15.7 mmol) and silver carbonate (3.96 g, 14.4 mmol). The flask was covered with aluminum foil, and after 85 hr, the mixture was diluted with ethyl acetate, filtered through celite, and concentrated in vacuo. The residue was purified via silica gel chromatography, eluting with 0-20% ethyl acetate in hexanes to provide methyl 6-(benzyloxy)pyridine-3-carboxylate.

Workup

  1. filtrationfiltered through celite
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified via silica gel chromatography
  4. washeluting with 0-20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-137ab7a07a0d424bbe37ae382baedb39
Source dataset
uspto-grants-2014_04
Patent number
US08697690B2

Reaction notes

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