Sodium Hydroxide → 2-Ethynyl-5-fluoropyridine
Reaction equation
C[C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]([C:9]#[C:10]CO)[C:3]=1C.[OH-].[Na+]>C1(C)C=CC=CC=1>[F:8][C:7]1[CH:2]=[CH:3][C:4]([C:9]#[CH:10])=[N:5][CH:6]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 120 °C
Procedure
820 mg (4.58 mmol) of Dimethylhydroxymethyl-5-fluoro-2-pyridylacetylene and 192 mg (4.81 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 0.25 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 90 mmHg/70° C. to give 5-fluoro-2-pyridylethyne as an orange-color liquid (0.35 g, yield: 63%).
Workup
- customequipped with a reflux condenser
- washthe mixture was washed with a saturated aqueous ammonium chloride solution
- dry with materialdried over magnesium sulfate
- distillationThe solvent was distilled off under reduced pressure at 90 mmHg/70° C.
Sources & evidence
- ORD record
- ord-b616b41a5165482b91a4c56b19786f92
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08137821B2
Reaction notes
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