Acetic Anhydride → HCID 11129341, compound

HRID 907388Notes

Reaction equation

HRID 907388 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[CH3:11][C:12]1[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][N:13]=1.C(OC(=O)C)(=O)C.C(OCC)(=O)C>[Cl-].[Na+].O.[Cl-].[Zn+2].[Cl-]>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6](/[CH:7]=[CH:11]/[C:12]2[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][N:13]=2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 312444-MethoxybenzaldehydeHCID 231548Methyl 6-methylnicotinate

Product 1

HCID 11129341HCID 11129341, compoundYield 21.3%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 57417360Sodium chloride; waterSolvent

Procedure

4-Methoxybenzaldehyde (210 mg, 1.52 mmol), methyl 6-methylnicotinate (230 mg, 1.52 mmol), acetic anhydride (310 mg, 3.04 mmol) and catalytic amount of zinc chloride were heated at 140° C. with stirring for 12 h. Ethyl acetate and brine were added to the cooled reaction mixture and the product was extracted. The organic layers were combined, dried (MgSO4) and the solvent removed under reduced pressure. The crude product was applied to a silica gel column and the product was eluted with ethyl acetate/n-hexane (1:1 RF=0.60 fluorescent under the UV lamp). Fractions containing the required product were collected and the solvents removed under reduced pressure to give the sub-title compound as a yellow solid (87 mg, 21%).

Workup

  1. extractionthe product was extracted
  2. dry with materialdried (MgSO4)
  3. customthe solvent removed under reduced pressure
  4. washthe product was eluted with ethyl acetate/n-hexane (1:1 RF=0.60 fluorescent under the UV lamp)
  5. additionFractions containing the required product
  6. customwere collected
  7. customthe solvents removed under reduced pressure

Sources & evidence

ORD record
ord-ea987f34a491465596fe7264b16db6c9
Source dataset
uspto-grants-2011_09
Patent number
US08012967B2

Reaction notes

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