Hydrochloric Acid → HCID 86593247, compound

HRID 1610428Notes

Reaction equation

HRID 1610428 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7](=[O:25])[CH:8]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.Cl>C(OCC)C.[BH4-].[Zn+2].[BH4-]>[Cl:1][C:2]1[S:6][C:5]([CH:7]([OH:25])[CH:8]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([C:21]([F:22])([F:23])[F:24])=[CH:19][CH:20]=2)[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 22261898HCID 22261898, compound

Product 1

HCID 86593247HCID 86593247, compound

Reagents, catalysts & solvents 2

HCID 12838295ZINC;boranuideCatalystHCID 3283Diethyl EtherSolvent

Procedure

While stirring zinc chloride (6.47 g, 47.5 mmol) in diethyl ether (100 ml), sodium borohydride (3.59 g, 94.9 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 (washed with diethyl ether) to give a solution of zinc borohydride in diethyl ether. To the obtained solution was added a solution of ethyl 3-(5-chloro-2-thienyl)-3-oxo-2-[4-(trifluoromethyl)benzyl]propionate (9.272 g, 23.73 mmol) in diethyl ether (50 ml) at room temperature, and the mixture was stirred as it was for 2 hrs. Dilute hydrochloric acid was added to the reaction solution by small portions to decompose excess zinc borohydride. 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=9/1-3/1) 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=9/1-3/1)
  6. customto give the objective substance

Sources & evidence

ORD record
ord-f2cc8a7e1e1d42c0a3b122d18de5e0b6
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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