Benzyl Alcohol → 3-(Benzyloxy)-6-chloropyridazine

HRID 1581498Notes

Reaction equation

HRID 1581498 reaction equation
[Na].[Cl:2][C:3]1[N:4]=[N:5][C:6](Cl)=[CH:7][CH:8]=1.[CH2:10]([OH:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[CH2:10]([O:17][C:6]1[N:5]=[N:4][C:3]([Cl:2])=[CH:8][CH:7]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 3

HCID 244Benzyl Alcohol2×HCID 673313,6-DichloropyridazineHCID 5360545Sodium2×

Product 1

HCID 225069573-(Benzyloxy)-6-chloropyridazineYield 90%

Procedure

Sodium metal (3.1 g) was added to benzyl alcohol (75 mL) and gently warmed to 50° C. for 30 minutes until all the sodium metal dissolved. A solution of 3,6-dichloropyridazine (135 mmol) in benzyl alcohol (75 mL) was added. The reaction mixture was kept at 100° C. for 24 hours. Excess benzyl alcohol was evaporated and the residue was extracted with ethyl acetate (3×100 mL) and the ethyl acetate extract was washed with water. The resulting ethyl acetate layer was collected, dried, filtered, and the filtrate was evaporated to afford the title compound (90%, 26.7 g); mp, 77-78° C.

Workup

  1. dissolutiondissolved
  2. customExcess benzyl alcohol was evaporated
  3. extractionthe residue was extracted with ethyl acetate (3×100 mL)
  4. extractionthe ethyl acetate extract
  5. washwas washed with water
  6. customThe resulting ethyl acetate layer was collected
  7. customdried
  8. filtrationfiltered
  9. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-785f4c590f7d47fa845cbe6dea1f13a5
Source dataset
uspto-grants-2004_05
Patent number
US06730674B2

Reaction notes

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