1-Hexanol → 3-[4-(Hexyloxy)-1,2,5-oxadiazol-3-yl]pyridine

HRID 1728755Notes

Reaction equation

HRID 1728755 reaction equation
[Na].Cl[C:3]1[C:4]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)=[N:5][O:6][N:7]=1.[CH2:14]([OH:20])[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]>>[CH2:14]([O:20][C:3]1[C:4]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)=[N:5][O:6][N:7]=1)[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

4

Reactant 3

HCID 81031-HexanolHCID 5360545SodiumHCID 15180172HCID 15180172, compound

Product 1

HCID 151801743-[4-(Hexyloxy)-1,2,5-oxadiazol-3-yl]pyridine

Conditions

Temperature
25 °C

Procedure

To a solution of sodium (100 mg, 4.3 mmol) in 1-hexanol (10 ml) was added 3-(4-chloro-1,2,5-oxadiazol-3-yl)pyridine (180 mg, 1 mmol). The mixture was stirred at 25° C. for 18 h and evaporated. The residue was dissolved in water and extracted with ether. The combined organic phases were dried and evaporated to give the title compound.

Workup

  1. customevaporated
  2. dissolutionThe residue was dissolved in water
  3. extractionextracted with ether
  4. customThe combined organic phases were dried
  5. customevaporated

Sources & evidence

ORD record
ord-bbe71350b53b4493995ef12a1489742b
Source dataset
uspto-grants-1994_07
Patent number
US05328925

Reaction notes

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