Reaction #955930

Reaction equation

3,6-dichloropyridazine

NaH

pyridin-2-ylmethanol

→

3-chloro-6-(pyridin-2-ylmethoxy)pyridazine

Yield 62.0%

Solvents

THF

Conditions

Workup

1. 1
   workup.STIRRINGthe mixture was stirred at 55° C. for 4 hours
2. 2
   OtherThe reaction was quenched with water and sat. NaHCO3
3. 3
   workup.ADDITIONwas added
4. 4
   ExtractionThe product was then extracted with EtOAc
5. 5
   Dryingdried over MgSO4
6. 6
   Filtrationfiltered
7. 7
   Otherevaporated
8. 8
   OtherThe residue was purified on silica gel(Eluent: 80% EtOAc in hexanes)

Procedure

To a solution of NaH (1.44 g, 36 mmol, 60% in mineral oil) in THF (15 mL) was added pyridin-2-ylmethanol (1.16 ml, 12 mmol) and the mixture was stirred for 30 min at rt. Then 3,6-dichloropyridazine (1.79 g, 14 mmol) was added and the mixture was stirred at 55° C. for 4 hours. The reaction was quenched with water and sat. NaHCO3 was added. The product was then extracted with EtOAc, dried over MgSO4 filtered and evaporated. The residue was purified on silica gel(Eluent: 80% EtOAc in hexanes) to give 3-chloro-6-(pyridin-2-ylmethoxy)pyridazine as a white solid (1.64 g, 62%). 1H NMR (300 MHz, dMSO): δ 5.57 (s, 2H), 7.35-7.38 (m, 1H), 7.48-7.54 (m, 2H), 7.82-7.88 (m, 2H), 8.57-8.59 (dd, 1H); MS (M+H, 222).

Source