Hydrochloric Acid → HCID 86593294, compound

HRID 1610690Notes

Reaction equation

HRID 1610690 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:28])[CH:9]([CH2:15][C:16]2[O:20][N:19]=[C:18]([O:21][C:22]([F:27])([F:26])[CH:23]([F:25])[F:24])[CH:17]=2)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.Cl>C(OCC)C.[BH4-].[Zn+2].[BH4-]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:28])[CH:9]([CH2:15][C:16]2[O:20][N:19]=[C:18]([O:21][C:22]([F:26])([F:27])[CH:23]([F:25])[F:24])[CH:17]=2)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 22261873HCID 22261873, compound

Product 1

HCID 86593294HCID 86593294, compound

Reagents, catalysts & solvents 2

HCID 12838295ZINC;boranuideCatalystHCID 3283Diethyl EtherSolvent

Procedure

While stirring zinc chloride (6.35 g, 46.6 mmol) in diethyl ether (100 ml), sodium borohydride (3.53 g, 93.2 mmol) was added at room temperature, and the mixture was stirred as it was for 2 hrs. The insoluble material of the mixture was removed by filtration and washed with diethyl ether to give a solution of zinc borohydride in diethyl ether. A solution of ethyl 3-(4-fluorophenyl)-3-oxo-2-[[3-(1,1,2,2-tetrafluoroethoxy)isoxazol-5-yl]methyl]propionate (2.372 g, 5.824 mmol) in diethyl ether (30 ml) was added to the obtained solution under ice-cooling, and the mixture was heated under reflux for 4 hrs. To the reaction solution was added dilute hydrochloric acid by small portions to decompose excess zinc borohydride, and the mixture was extracted twice with ethyl acetate. The recovered organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (hexane/ethyl acetate=6/1−3/1) to give the objective substance.

Workup

  1. temperaturecooling
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 4 hrs
  4. extractionthe mixture was extracted twice with ethyl acetate
  5. dry with materialThe recovered organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained crude product
  8. customwas purified by silica gel column chromatography (hexane/ethyl acetate=6/1−3/1)
  9. customto give the objective substance

Sources & evidence

ORD record
ord-6bcdf42e39d8499c90e61b83dd853dc4
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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