Water → HCID 57815358, compound

HRID 385584Notes

Reaction equation

HRID 385584 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH:11]=[C:10](OS(C(F)(F)F)(=O)=O)[C:9]([O:20][CH3:21])=[CH:8][N:7]=1)(=[O:3])[CH3:2].[C:22](=O)([O-])[O-].[K+].[K+].CB1OB(C)OB(C)O1.O>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OCC)(=O)C>[C:1]([O:4][CH2:5][C:6]1[CH:11]=[C:10]([CH3:22])[C:9]([O:20][CH3:21])=[CH:8][N:7]=1)(=[O:3])[CH3:2]

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 57815175HCID 57815175, compound

Product 1

HCID 57815358HCID 57815358, compoundYield 74.2%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 0.50 g of (5-methoxy-4-(((trifluoromethyl)sulfonyl)oxy)pyridin-2-yl)methyl acetate in 5 mL of dioxane, 0.63 g of potassium carbonate, 0.21 mL of trimethylboroxin and 0.18 g of tetrakis(triphenylphosphine)palladium(0) were added, and the mixture was stirred at 70 to 90° C. for 3 hours under a nitrogen atmosphere. The mixture was heated under reflux while further stirring for 3 hours, after cooling to room temperature, water and ethyl acetate were added to the reaction mixture, and the organic layer was separated. The aqueous layer was extracted with ethyl acetate, the organic layer and the extract were combined, the resultant solution was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resultant residue was purified by flash silica gel column chromatography using gradient elution with hexane:ethyl acetate=80:20 to 50:50 to obtain 0.22 g of (5-methoxy-4-methylpyridin-2-yl)methyl acetate as a yellow oily substance.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux
  3. stirringwhile further stirring for 3 hours
  4. temperatureafter cooling to room temperature
  5. customthe organic layer was separated
  6. extractionThe aqueous layer was extracted with ethyl acetate
  7. dry with materialthe resultant solution was dried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe resultant residue was purified by flash silica gel column chromatography
  10. washelution with hexane

Sources & evidence

ORD record
ord-b0cbd9d442eb4faf93e38e7e9e9f08f1
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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