Hydrochloric Acid → HCID 86593289, compound

HRID 1610663Notes

Reaction equation

HRID 1610663 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7](=[O:28])[CH:8]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]([F:27])([F:26])[CH:23]([F:25])[F:24])[CH:16]=2)[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1.Cl>[BH4-].[Zn+2].[BH4-]>[Cl:1][C:2]1[S:6][C:5]([CH:7]([OH:28])[CH:8]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]([F:26])([F:27])[CH:23]([F:24])[F:25])[CH:16]=2)[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22261890HCID 22261890, compound

Product 1

HCID 86593289HCID 86593289, compound

Reagents, catalysts & solvents 1

HCID 12838295ZINC;boranuideCatalyst

Procedure

While stirring zinc chloride (7.76 g, 57.0 mmol) in diethyl ether (150 ml), sodium borohydride (4.31 g, 114 mmol) was added at room temperature, and the mixture was stirred at 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. To the obtained solution was added ethyl 3-(5-chloro-2-thienyl)-3-oxo-2-[3-(1,1,2,2-tetrafluoroethoxy)benzyl]propionate (12.50 g, 28.48 mmol) under ice-cooling, and the mixture was stirred at room temperature for 2 hrs. To the reaction solution was added dilute hydrochloric acid by small portions to decompose excess zinc borohydride. 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=6/1−1/1) to give the objective substance.

Workup

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

Sources & evidence

ORD record
ord-9a2895714b3f4804a41104ff7a9c0d6e
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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