Sodium Hydroxide → 5-Ethynyl-2-fluoropyridine

HRID 1095214Notes

Reaction equation

HRID 1095214 reaction equation
C[C:2]1[C:7]([C:8]#[C:9]CO)=[CH:6][N:5]=[C:4]([F:12])[C:3]=1C.[OH-].[Na+]>C1(C)C=CC=CC=1>[F:12][C:4]1[N:5]=[CH:6][C:7]([C:8]#[CH:9])=[CH:2][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66783791HCID 66783791, compound

Product 1

HCID 468357115-Ethynyl-2-fluoropyridineYield 32.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
120 °C

Procedure

0.830 mg (4.63 mmol) of Dimethylhydroxymethyl-2-fluoro-5-pyridylacetylene and 195 mg (4.86 mmol) of NaOH (KISHIDA CHEMICAL CO., Ltd., 0.7 mm granular, 98%) were placed in a 50 mL two-neck flask equipped with a reflux condenser and the air inside the flask was replaced with Ar. 23 mL of toluene was added thereto and the mixture was refluxed at 120° C. for 1 hour. Toluene was added to the reaction mixture and the mixture was washed with a saturated aqueous ammonium chloride solution and dried over magnesium sulfate. The solvent was distilled off under reduced pressure at 95 mmHg/72° C. to give 6-fluoro-3-pyridylethyne as an orange-color liquid (0.18 g, yield: 32%).

Workup

  1. customequipped with a reflux condenser
  2. washthe mixture was washed with a saturated aqueous ammonium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure at 95 mmHg/72° C.

Sources & evidence

ORD record
ord-b34ce0ef858c459c86911c1d2e50b009
Source dataset
uspto-grants-2012_03
Patent number
US08137821B2

Reaction notes

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