Water → HCID 10488012, compound

HRID 1913274Notes

Reaction equation

HRID 1913274 reaction equation
C(=O)([O-])[O-].[K+].[K+].[N:7]1[CH:12]=[CH:11][CH:10]=[C:9]([OH:13])[CH:8]=1.C([O:16][CH:17](O)[C:18]([F:21])([F:20])[F:19])C.O>C(OCC)(=O)C>[F:19][C:18]([F:21])([F:20])[CH:17]([C:12]1[N:7]=[CH:8][C:9]([OH:13])=[CH:10][CH:11]=1)[OH:16]

Participants

6

Reactant 4

HCID 962WaterHCID 79713-HydroxypyridineHCID 9897Ethanol, 1-ethoxy-2,2,2-trifluoro-HCID 11430Potassium Carbonate

Product 1

HCID 10488012HCID 10488012, compoundYield 19.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

Potassium carbonate (4.66 g, 36.3 mmol) was added to the mixture of pyridin-3-ol (2.00 g, 21.0 mmol) and 1-ethoxy-2,2,2-trifluoroethanol (3.30 g, 23.1 mmol), and the mixture was stirred for 4 hours at 100° C. under nitrogen atmosphere. This reaction solution was cooled to room temperature, followed by adding water and ethyl acetate to the reaction solution, washing the organic layer with a saturated saline solution, drying the layer with anhydrous sodium sulfate, and thereafter concentration under reduced pressure. The obtained residue was purified by silica gel column chromatography (Purif-Pack SI200, hexane:ethyl acetate:=40:60) to obtain the title compound (780 mg, yield: 19%) as a white amorphous.

Workup

  1. temperatureThis reaction solution was cooled to room temperature
  2. washwashing the organic layer with a saturated saline solution
  3. dry with materialdrying the layer with anhydrous sodium sulfate
  4. concentrationconcentration under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (Purif-Pack SI200, hexane:ethyl acetate:=40:60)

Sources & evidence

ORD record
ord-5bff0dc5626b45bf9321299709c1e7f4
Source dataset
uspto-grants-2013_12
Patent number
US08609699B2

Reaction notes

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