Chloroform → 3,5-Dimethyl-4-(2,2,3,3,3-pentafluoropropoxy)pyridine-1-oxide

HRID 622157Notes

Reaction equation

HRID 622157 reaction equation
[CH3:1][C:2]1[CH:3]=[N+:4]([O-:12])[CH:5]=[C:6]([CH3:11])[C:7]=1[N+]([O-])=O.CC(C)([O-])C.[K+].C(Cl)(Cl)Cl.[F:23][C:24]([F:31])([C:27]([F:30])([F:29])[F:28])[CH2:25][OH:26]>>[CH3:1][C:2]1[CH:3]=[N+:4]([O-:12])[CH:5]=[C:6]([CH3:11])[C:7]=1[O:26][CH2:25][C:24]([F:31])([F:23])[C:27]([F:30])([F:29])[F:28]

Participants

5

Reactant 4

HCID 6212ChloroformHCID 98722,2,3,3,3-PentafluoropropanolHCID 96264Pyridine, 3,5-dimethyl-4-nitro-, 1-oxideHCID 23665647Potassium tert-butoxide

Product 1

HCID 136548073,5-Dimethyl-4-(2,2,3,3,3-pentafluoropropoxy)pyridine-1-oxideYield 80.6%

Conditions

Temperature
60 °C

Procedure

To a solution of 3,5-dimethyl-4-nitropyridine-1-oxide (2.0 g) in 2,2,3,3,3-pentafluoropropanol (10 g), potassium t-butoxide (2 g) was added gradually at 0° C. over a period of 15 minutes, after which the solution was stirred at 60° C. for 18 hours. The resulting reaction product, after adding chloroform, was subjected to Celite filtration, after which the filtrate was applied on a silica gel (80 g) column, was eluted with ethyl acetate-hexane (1:1) and then with 20% methanol-ethyl acetate and then recrystallized from ether-hexane to give 2.6 g of 3.5-dimethyl-4-(2,2,3,3,3-pentafluoropropoxy)pyridine-1-oxide as crystals (melting point: 89°~91° C.).

Workup

  1. customThe resulting reaction product
  2. filtrationwas subjected to Celite filtration
  3. washwas eluted with ethyl acetate-hexane (1:1)
  4. customwith 20% methanol-ethyl acetate and then recrystallized from ether-hexane

Sources & evidence

ORD record
ord-28145a7efee64baeb91f15c61bd85d18
Source dataset
uspto-grants-1988_09
Patent number
US04769456

Reaction notes

Loading…