Trifluoromethanesulfonic anhydride → 5-Methyl-3-(3-allyl-4-trifluoromethylsulphonyloxyphenyl)-1,2,4-oxadiazole

HRID 861431Notes

Reaction equation

HRID 861431 reaction equation
[S:1]([O:8]S(C(F)(F)F)(=O)=O)([C:4]([F:7])([F:6])[F:5])(=[O:3])=[O:2].[CH3:16][C:17]1[O:21][N:20]=[C:19]([C:22]2[CH:27]=[CH:26][C:25](O)=[C:24]([CH2:29][CH:30]=[CH2:31])[CH:23]=2)[N:18]=1>N1C=CC=CC=1.Cl>[CH3:16][C:17]1[O:21][N:20]=[C:19]([C:22]2[CH:27]=[CH:26][C:25]([O:8][S:1]([C:4]([F:7])([F:6])[F:5])(=[O:3])=[O:2])=[C:24]([CH2:29][CH:30]=[CH2:31])[CH:23]=2)[N:18]=1

Participants

5

Reactant 2

HCID 67749Trifluoromethanesulfonic anhydrideHCID 1360822352-Allyl-4-(5-methyl-1,2,4-oxadiazol-3-yl)phenol

Product 1

HCID 197031335-Methyl-3-(3-allyl-4-trifluoromethylsulphonyloxyphenyl)-1,2,4-oxadiazole

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 1049PyridineSolvent

Procedure

Triflic anhydride (1.4 ml) was added dropwise to a stirred solution of 5-methyl-3-(3-allyl-4-hydroxyphenyl)1,2,4-oxadiazole (1.2 g) in pyridine (10 ml) cooled in an ice-bath. The mixture was stirred for 45 minutes. The mixture was diluted with 1M aqueous hydrochloric acid (200 ml) and extracted with ethyl acetate (200 ml). The organic extract was washed with 1M aqueous hydrochloric acid, aqueous sodium bicarbonate solution, and brine, then dried (MgSO4), and evaporated to give 5-methyl-3-(3-allyl-4-trifluoromethylsulphonyloxyphenyl)-1,2,4-oxadiazole (1.37 g) as a solid, NMR: 8.1(2H,m), 7.6(1H,d), 6.1-5.9(1H,m), 5.3-5.1(2H,m), 3.55(2H,d) and 2.7(3H,s); m/z 351 (M+H).

Workup

  1. temperaturecooled in an ice-bath
  2. extractionextracted with ethyl acetate (200 ml)
  3. extractionThe organic extract
  4. washwas washed with 1M aqueous hydrochloric acid, aqueous sodium bicarbonate solution, and brine
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-37ec86091db041979fe4651cbb520de3
Source dataset
uspto-grants-1998_02
Patent number
US05714496

Reaction notes

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