Hydrochloric Acid → HCID 22262356, compound

HRID 1610536Notes

Reaction equation

HRID 1610536 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([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:7]=[CH:8][CH:9]=1.Cl.O>C(OCC)C.[Cl-].[Zn+2].[Cl-]>[F:3][C:4]1[CH:5]=[C:6]([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:7]=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 22261547HCID 22261547, compound

Product 1

HCID 22262356HCID 22262356, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of zinc chloride (5.60 g, 41.1 mmol) in diethyl ether (140 ml) was added sodium borohydride (3.11 g, 82.2 mmol), and the mixture was stirred at room temperature for 30 min. Insoluble material was filtered off. To the filtrate was added a solution of ethyl 3-(3-fluorophenyl)-3-oxo-2-[3-(1,1,2,2-tetrafluoroethoxy)benzyl]propanoate (8.56 g, 20.6 mmol) in diethyl ether (50 ml) at 0° C., and the mixture was stirred for 30 min. 1N Hydrochloric acid was added to the reaction solution to stop the reaction. Then, water (100 ml) was added and the mixture was extracted with ethyl acetate (200 ml×2). The extract was washed with water and saturated brine, dried (anhydrous magnesium sulfate), and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to give the objective substance (7.04 g, 82%) as a colorless oil.

Workup

  1. filtrationInsoluble material was filtered off
  2. stirringthe mixture was stirred for 30 min
  3. customthe reaction
  4. extractionthe mixture was extracted with ethyl acetate (200 ml×2)
  5. washThe extract was washed with water and saturated brine
  6. dry with materialdried (anhydrous magnesium sulfate)
  7. customevaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)
  9. customto give the objective substance (7.04 g, 82%) as a colorless oil

Sources & evidence

ORD record
ord-e23f09679a654bd09c3da7ffb8ff865b
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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