Chloroform → 3,5-Dimethyl-4-(2,2,3,3,3-pentafluoropropoxy)pyridine-1-oxide
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
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) was added at 0° C. little by little potassium t-butoxide (2 g) over 15 minutes. The mixture was stirred at 60° C. for 18 hours. To the reaction mixture was added chloroform, which was subjected to filtration with celite. The filtrate was chromatographed on a column of silica gel (80 g), eluted with ethyl acetate-hexane (1:1), then with 20% methanol-ethyl acetate, and recrystallized from ether-hexane to yield 2.6 g of 3,5-dimethyl-4-(2,2,3,3,3-pentafluoropropoxy)pyridine-1-oxide as crystals, m.p. 89°-91° C.
Workup
- filtrationwas subjected to filtration with celite
- customThe filtrate was chromatographed on a column of silica gel (80 g)
- washeluted with ethyl acetate-hexane (1:1)
- customwith 20% methanol-ethyl acetate, and recrystallized from ether-hexane
Sources & evidence
- ORD record
- ord-3d944872a4c84c12aebb7d0274d5ef22
- Source dataset
- uspto-grants-1987_08
- Patent number
- US04689333
Reaction notes
Loading…