Hydrochloric Acid → HCID 86593296, compound

HRID 1610694Notes

Reaction equation

HRID 1610694 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:25])[CH:9]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH:22]([CH3:24])[CH3:23])[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:25])[CH:9]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH:22]([CH3:24])[CH3:23])[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 22262262HCID 22262262, compound

Product 1

HCID 86593296HCID 86593296, compound

Reagents, catalysts & solvents 2

HCID 12838295ZINC;boranuideCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

While stirring zinc chloride (3.99 g, 29.3 mmol) in diethyl ether (30 ml), sodium borohydride (2.22 g, 58.6 mmol) was added at room temperature, and the mixture was stirred as it was for 2 hrs. The insoluble material in 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 a solution of ethyl 3-(4-fluorophenyl)-2-(3-isopropylbenzyl)-3-oxopropionate (5.016 g, 14.65 mmol) in diethyl ether (30 ml) under ice-cooling, and the mixture was stirred at 0° C. for 20 min. 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. 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=6/1−3/1)
  7. customto give the objective substance

Sources & evidence

ORD record
ord-7074fac1477240ce9bd79f9d71c1e0c0
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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