Hydrochloric Acid → HCID 86593234, compound

HRID 1610338Notes

Reaction equation

HRID 1610338 reaction equation
[F:1][CH:2]([F:25])[C:3]1[CH:24]=[CH:23][C:6]([CH2:7][CH:8]([C:14]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[O:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:5][CH:4]=1.Cl>C(OCC)C.[BH4-].[Zn+2].[BH4-]>[F:25][CH:2]([F:1])[C:3]1[CH:24]=[CH:23][C:6]([CH2:7][CH:8]([CH:14]([C:16]2[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=2)[OH:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 22261564HCID 22261564, compound

Product 1

HCID 86593234HCID 86593234, compound

Reagents, catalysts & solvents 2

HCID 12838295ZINC;boranuideCatalystHCID 3283Diethyl EtherSolvent

Procedure

While stirring zinc chloride (2.17 g, 16.0 mmol) in diethyl ether (50 ml), sodium borohydride (1.21 g, 31.9 mmol) as 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 (washed with diethyl ether) to give a solution of zinc borohydride in diethyl ether. To the obtained solution was added a solution of ethyl 2-[4-(difluoromethyl)benzyl]-3-(4-fluorophenyl)-3-oxopropionate (2.794 g, 7.975 mmol) in diethyl ether (30 ml) at room temperature and the mixture was stirred as it was for 2 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 collected 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. extractionthe mixture was extracted twice with ethyl acetate
  2. dry with materialThe collected organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe obtained crude product
  5. customwas purified by silica gel column chromatography (hexane/ethyl acetate=6/1−3/1)
  6. customto give the objective substance

Sources & evidence

ORD record
ord-120e27bd24674a5d8d63eb1fa31a8200
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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