Tetrahydrofuran → HCID 86646559, compound

HRID 454822Notes

Reaction equation

HRID 454822 reaction equation
O1CCCC1.[H-].[Na+].[Cl:8][C:9]1[N:10]=[N:11][C:12](Cl)=[CH:13][CH:14]=1.[F:16][CH2:17][CH2:18][OH:19]>O>[F:16][CH2:17][CH2:18][O:19][C:12]1[N:11]=[N:10][C:9]([Cl:8])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 97372-FluoroethanolHCID 24758Sodium hydrideHCID 673313,6-Dichloropyridazine

Product 1

HCID 86646559HCID 86646559, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To anhydrous tetrahydrofuran (5 mL) containing sodium hydride (NaH 60%, 121 mg, 3.02 mmol) was slowly added anhydrous tetrahydrofuran (2 mL) having 3,6-dichloropyridazine (107, 300 mg, 2.01 mmol) dissolved therein at 0° C., and added dropwise 2-fluoroethanol (194 mg, 3.02 mmol). The reaction mixture was stirred for one minutes and water was carefully added. Organic compounds were extracted with ethyl acetate, and the recovered organic solution was washed with an aqueous solution of saturated sodium chloride and evaporated after a treatment with sodium sulfate. Purification was performed by column chromatograph to give the target compound 3-(2-fluoroethoxy)-6-chloropyridazine (108b, 295 mg, 83%) as a white solid.

Workup

  1. dissolutiondissolved
  2. extractionOrganic compounds were extracted with ethyl acetate
  3. washthe recovered organic solution was washed with an aqueous solution of saturated sodium chloride
  4. customevaporated after a treatment with sodium sulfate
  5. customPurification

Sources & evidence

ORD record
ord-7ae071ce5da14e2593dea49963f730b2
Source dataset
uspto-grants-2013_07
Patent number
US08497260B2

Reaction notes

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