4-Methyloxybenzyl chloride → HCID 86658014, compound

HRID 70713Notes

Reaction equation

HRID 70713 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Cl)=[CH:5][CH:4]=1.[CH:11]1([C:14]2[C:19](=[O:20])[NH:18][C:17]([CH:21]=[O:22])=[CH:16][CH:15]=2)[CH2:13][CH2:12]1.[Al]>C(Cl)(Cl)Cl.C(=O)([O-])[O-].[Ag+2]>[CH:11]1([C:14]2[CH:15]=[CH:16][C:17]([CH:21]=[O:22])=[N:18][C:19]=2[O:20][CH2:7][C:6]2[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH2:13][CH2:12]1

Participants

6

Reactant 3

HCID 699934-Methyloxybenzyl chlorideHCID 5359268AluminumHCID 866580135-Cyclopropyl-6-oxo-1,6-dihydropyridine-2-carbaldehyde

Product 1

HCID 86658014HCID 86658014, compoundYield 105.3%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 6212ChloroformSolvent

Procedure

p-Methoxybenzyl chloride (329 mg) was added to a solution of 5-cyclopropyl-6-oxo-1,6-dihydropyridine-2-carbaldehyde (228 mg) in chloroform (10 mL), after which the reaction tube was covered with aluminum foil to provide shading conditions. Silver carbonate (771 mg) was added and the mixture was stirred at room temperature for three hours. The insoluble matter was filtered off and then the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=92:8→34:66) to give 5-cyclopropyl-6-[(4-methoxybenzyl)oxy]pyridine-2-carbaldehyde as a colorless oil (417 mg, 86%).

Workup

  1. customto provide shading conditions
  2. filtrationThe insoluble matter was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=92:8→34:66)

Sources & evidence

ORD record
ord-c572a8a4b46340c5917b7d7882651cf1
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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