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

HRID 22760

Reaction equation

HRID 22760 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%

Conditions

Temperature
100 °C

Procedure

Sodium metal (130 mmol, 3.1 g) was added to benzyl alcohol (75 mL) and gently warmed to 50° C. for 30 minutes until all the sodium metal had dissolved. To this was added a solution of 3,6-dichloropyridazine (135 mmol) in benzyl alcohol (75 mL). The reaction was heated at 100° C. for 24 h. Excess benzyl alcohol was evaporated and the residue was extracted with EtOAc (3×100 mL). The EtOAc extract was washed with H2O. The EtOAc layer was collected, dried, filtered and the filtrate was evaporated to yield 3-benzyloxy-6-chloro-pyridazine (90%, 26.7 g); mp 77° C.-78° C.

Workup

  1. dissolutionhad dissolved
  2. customExcess benzyl alcohol was evaporated
  3. extractionthe residue was extracted with EtOAc (3×100 mL)
  4. extractionThe EtOAc extract
  5. washwas washed with H2O
  6. customThe EtOAc layer was collected
  7. customdried
  8. filtrationfiltered
  9. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-67dfb63943c64437b68524ce4d03319d
Source dataset
uspto-grants-2005_02
Patent number
US06849629B2

Linked notes

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