Dichloromethane → 2,3,3-Trifluoro-1-(4'-Ethoxy-2',3'-Difluorophenyl)carbonyloxy-4-n-Propylbicyclo[2.2.2]octane

HRID 1644128Notes

Reaction equation

HRID 1644128 reaction equation
C(Cl)Cl.[CH2:4]([O:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[C:9]([F:16])[C:8]=1[F:17])[CH3:5].[F:18][CH:19]1[C:24]([F:26])([F:25])[C:23]2([CH2:29][CH2:30][CH3:31])[CH2:27][CH2:28][C:20]1(O)[CH2:21][CH2:22]2.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.O>[F:18][CH:19]1[C:24]([F:25])([F:26])[C:23]2([CH2:29][CH2:30][CH3:31])[CH2:22][CH2:21][C:20]1([O:12][C:11]([C:10]1[CH:14]=[CH:15][C:7]([O:6][CH2:4][CH3:5])=[C:8]([F:17])[C:9]=1[F:16])=[O:13])[CH2:28][CH2:27]2

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10868DicyclohexylcarbodiimideHCID 27694004-Ethoxy-2,3-difluorobenzoic acidHCID 594808822,3,3-Trifluoro-1-Hydroxy-4-n-Propylbicyclo[2.2.2]octane

Product 1

HCID 594809002,3,3-Trifluoro-1-(4'-Ethoxy-2',3'-Difluorophenyl)carbonyloxy-4-n-Propylbicyclo[2.2.2]octane

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Procedure

Methylene chloride solution containing 4-ethoxy-2,3-difluorobenzoic acid (7) (52.6 mg) and 2,3,3-trifluoro-1-hydroxy-4-n-propylbicyclo[2.2.2]octane (4) (39.0 mg) was added with N,N′-dicyclohexyl carbodiimide (53.0 mg) and 4-dimethylamino pyridine (7.0 mg), and the mixture was refluxed under heating for 11 hours. The mixture was then added with water to terminate the reaction, the organic layer was extracted three times with ethyl acetate, the organic layers were combined, and the combined organic layer was washed with saturated sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate, and the solvent was then vaporized off under reduced pressure to thereby obtain a crude product. The crude product was purified by silica gel column chromatography (hexane/ethyl acetate=8:2), to thereby obtain 2,3,3-trifluoro-1-(4′-ethoxy-2′,3′-difluorophenyl)carbonyloxy-4-n-propylbicyclo[2.2.2]octane (8) (yield=20.0 mg, yield ratio=28%) as a colorless clear crystal.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 11 hours
  3. customto terminate
  4. customthe reaction
  5. extractionthe organic layer was extracted three times with ethyl acetate
  6. washthe combined organic layer was washed with saturated sodium chloride solution
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-d412bc75df1248b3b07a01305409eae3
Source dataset
uspto-grants-2012_02
Patent number
US08124196B2

Reaction notes

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