Hydrochloric Acid → HCID 86593290, compound

HRID 1610668Notes

Reaction equation

HRID 1610668 reaction equation
[BH4-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:31])[CH:11]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][C:25]([F:30])([F:29])[CH:26]([F:28])[F:27])[CH:19]=2)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][CH:5]=1.Cl>C(OCC)C>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([OH:31])[CH:11]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][C:25]([F:30])([F:29])[CH:26]([F:28])[F:27])[CH:19]=2)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 22261430HCID 22261430, compound

Product 1

HCID 86593290HCID 86593290, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of anhydride zinc chloride (11.4 g, 83.8 mmol) in diethyl ether (200 ml) was added sodium borohydride (6.34 g, 168 mmol) by small portions, and the mixture was stirred for 2 hrs. The insoluble material was removed by filtration and washed with diethyl ether. The filtrate was ice-cooled, and a solution of ethyl 3-(4-bromophenyl)-3-oxo-2-[3-(1,1,2,2-tetrafluoroethoxy)benzyl]propanoate (20 g, 41.9 mmol) in diethyl ether (50 ml) was added. The mixture was stirred at room temperature for 2 hrs. After cooling again, 2N hydrochloric acid was added to terminate the reaction. The obtained mixture was extracted with ethyl acetate (200, 100 ml), washed with water, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane:ethyl acetate=5:1-2:1) to give the objective substance (20 g, quantitative) as a colorless oil.

Workup

  1. customThe insoluble material was removed by filtration
  2. washwashed with diethyl ether
  3. temperaturecooled
  4. stirringThe mixture was stirred at room temperature for 2 hrs
  5. temperatureAfter cooling again
  6. customto terminate
  7. customthe reaction
  8. extractionThe obtained mixture was extracted with ethyl acetate (200, 100 ml)
  9. washwashed with water
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customevaporated under reduced pressure
  12. customThe residue was purified by silica gel chromatography (hexane:ethyl acetate=5:1-2:1)
  13. customto give the objective substance (20 g, quantitative) as a colorless oil

Sources & evidence

ORD record
ord-9b08b89dc04244c5a13b484e9a53a9e8
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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