Ethyl Acetate → HCID 86062444, compound

HRID 1696962Notes

Reaction equation

HRID 1696962 reaction equation
[H-].[Na+].[F:3][C:4]([F:12])([F:11])[CH:5]([OH:10])[C:6]([F:9])([F:8])[F:7].Cl[C:14]1[CH:19]=[C:18]([CH3:20])[C:17]([N+:21]([O-:23])=[O:22])=[CH:16][N:15]=1.C(OCC)(=O)C>O1CCCC1.O>[CH3:20][C:18]1[C:17]([N+:21]([O-:23])=[O:22])=[CH:16][N:15]=[C:14]([O:10][CH:5]([C:6]([F:9])([F:8])[F:7])[C:4]([F:12])([F:11])[F:3])[CH:19]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 135291,1,1,3,3,3-Hexafluoro-2-propanolHCID 24758Sodium hydrideHCID 3453642-Chloro-4-methyl-5-nitropyridine

Product 1

HCID 86062444HCID 86062444, compoundYield 85.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

1.33 g of 60% sodium hydride was introduced to 15 ml of tetrahydrofuran, the mixture was cooled down to 5 degree centigrade, and then 5.84 g of 1,1,1,3,3,3-hexafluoro-2-propanol wad added dropwise thereto. The resulting solution was stirred at 5 degree centigrade for 30 minutes, and then 3.0 g of 2-chloro-4-methyl-5-nitropyridine dissolved in 10 ml of tetrahydrofuran was added dropwise thereto, and stirred at room temperature for 3 hours. The solution was allowed to stand at room temperature for 3 days, and then ethyl acetate and water were added thereto. An organic layer was separated, washed with saturated salt water, and dried over anhydrous magnesium sulfate. Then, the solvent was removed under a reduced pressure to obtain a residue. The resulting residue was purified by silica gel column chromatography using an eluent (development solvent; hexane ethyl acetate=10:1) to obtain 4.5 g of the desired product (Yield: 80%) as yellow oil.

Workup

  1. temperaturethe mixture was cooled down to 5 degree centigrade
  2. additionwas added dropwise
  3. stirringstirred at room temperature for 3 hours
  4. waitto stand at room temperature for 3 days
  5. customAn organic layer was separated
  6. washwashed with saturated salt water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThen, the solvent was removed under a reduced pressure
  9. customto obtain a residue
  10. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d47b520fe82c4a8db94fd3d3fbe218cd
Source dataset
uspto-grants-2012_04
Patent number
US08163804B2

Reaction notes

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