Sodium Bicarbonate → Acetic acid 2-benzo[1,3]dioxol-5-yl-1-(6-methyl-pyridin-2-yl)-2-oxo-ethyl ester

HRID 917670Notes

Reaction equation

HRID 917670 reaction equation
[Br-].[O:2]1[C:6]2[CH:7]=[CH:8][C:9]([C:11](=[O:21])[CH:12]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[NH+:15]=3)Br)=[CH:10][C:5]=2[O:4][CH2:3]1.[C:22]([O-:25])(=[O:24])[CH3:23].[K+].C(=O)([O-])O.[Na+]>CN(C)C=O>[O:2]1[C:6]2[CH:7]=[CH:8][C:9]([C:11](=[O:21])[CH:12]([O:25][C:22](=[O:24])[CH3:23])[C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[N:15]=3)=[CH:10][C:5]=2[O:4][CH2:3]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 517044Potassium AcetateHCID 865927612-(2-Benzo[1,3]dioxol-5-yl-1-bromo-2-oxo-ethyl)-6-methyl-pyridinium bromide

Product 1

HCID 68886008Acetic acid 2-benzo[1,3]dioxol-5-yl-1-(6-methyl-pyridin-2-yl)-2-oxo-ethyl esterYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(2-benzo[1,3]dioxol-5-yl-1-bromo-2-oxo-ethyl)-6-methyl-pyridinium bromide (150 mg, 0.36 mmol), and potassium acetate (70 mg, 0.72 mmol, 2 equiv) in dimethylformamide (2 mL) was heated to 60° C. for 1 hour. The resulting reaction mixture was cooled to ambient temperature, treated with saturated aqueous sodium hydrogen carbonate, and extracted with ethyl acetate. The organics were washed with brine, dried with magnesium sulfate and concentrated in vacuo to provide acetic acid 2-benzo[1,3]dioxol-5-yl-1-(6-methyl-pyridin-2-yl)-2-oxo-ethyl ester (80 mg, 71%).

Workup

  1. customThe resulting reaction mixture
  2. extractionextracted with ethyl acetate
  3. washThe organics were washed with brine
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fad2219591d14bb688b046bbb4a9f098
Source dataset
uspto-grants-2007_09
Patent number
US07273936B2

Reaction notes

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