Tetrahydrofuran → 3-Chloro-6-methoxypyridazine

HRID 454821

Reaction equation

HRID 454821 reaction equation
CO.C[O-].[Na+].[O:6]1CCC[CH2:7]1.[Cl:11][C:12]1[N:13]=[N:14][C:15](Cl)=[CH:16][CH:17]=1>O>[CH3:7][O:6][C:15]1[N:14]=[N:13][C:12]([Cl:11])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 673313,6-DichloropyridazineHCID 23694274Sodium methanolate methanol

Product 1

HCID 744033-Chloro-6-methoxypyridazineYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 0.5 M sodium methoxide methanol solution (NaOMe in MeOH, 7.4 mL, 3.69 mmol) was slowly added to an anhydrous tetrahydrofuran (12 mL) solution having 3,6-dichloropyridazine (107, 500 mg, 3.36 mmol) dissolved therein, stirred at room temperature for one hour, followed by adding water. Organic compounds were extracted with ethyl acetate. Then, 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-methoxy-6-chloropyridazine (108a, 436 mg, 90%) as a white solid.

Workup

  1. dissolutiondissolved
  2. extractionOrganic compounds were extracted with ethyl acetate
  3. washThen, the 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-f94eb002897047a8bebf9c0993e81a45
Source dataset
uspto-grants-2013_07
Patent number
US08497260B2

Linked notes

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