Tetrahydrofuran → 2-Cyclopropyl-7-fluoro-5-fluoromethyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

HRID 17581Notes

Reaction equation

HRID 17581 reaction equation
[F-:1].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.Br[CH2:25][C:26]1[C:37]([C:38]#[N:39])=[C:30]2[N:31]=[C:32]([CH:34]3[CH2:36][CH2:35]3)[O:33][C:29]2=[C:28]([F:40])[C:27]=1[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1>O>[CH:34]1([C:32]2[O:33][C:29]3[C:30](=[C:37]([C:38]#[N:39])[C:26]([CH2:25][F:1])=[C:27]([C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=4)[C:28]=3[F:40])[N:31]=2)[CH2:36][CH2:35]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 685850015-Bromomethyl-2-cyclopropyl-7-fluoro-6-phenyl-1,3-benzoxazole-4-carbonitrile

Product 1

HCID 685846532-Cyclopropyl-7-fluoro-5-fluoromethyl-6-phenyl-1,3-benzoxazole-4-carbonitrileYield 59.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under nitrogen atmosphere at 0° C., tetra(n-butyl)ammonium fluoride (1.0 M tetrahydrofuran solution) (1.50 ml, 1.50 mmol) was added to a tetrahydrofuran (12 ml) solution of 5-bromomethyl-2-cyclopropyl-7-fluoro-6-phenyl-1,3-benzoxazole-4-carbonitrile (I-292) (426 mg, 1.15 mmol), followed by stirring with cooling with water for 1.5 hours. The solvent was evaporated away under reduced pressure, then the resulting residue was purified by middle-pressure liquid chromatography (eluent, n-hexane:ethyl acetate=4:1, v/v) to obtain the entitled compound (212 mg, 59%) as a colorless oil.

Workup

  1. customThe solvent was evaporated away under reduced pressure
  2. customthe resulting residue was purified by middle-pressure liquid chromatography (eluent, n-hexane

Sources & evidence

ORD record
ord-17f4aa60eaf0484c8107ad5e6d4452a2
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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