Hydrochloric Acid → HCID 86593280, compound

HRID 1610619Notes

Reaction equation

HRID 1610619 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:32])[CH:11]([CH2:17][C:18]2[CH:31]=[CH:30][C:21]3[O:22][C:23]([F:29])([F:28])[C:24]([F:27])([F:26])[O:25][C:20]=3[CH:19]=2)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][CH:5]=1.Cl.C(=O)([O-])O.[Na+]>C(OCC)C.[Cl-].[Zn+2].[Cl-].O>[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([OH:32])[CH:11]([CH2:17][C:18]2[CH:31]=[CH:30][C:21]3[O:22][C:23]([F:28])([F:29])[C:24]([F:27])([F:26])[O:25][C:20]=3[CH:19]=2)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][CH:5]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 22261776HCID 22261776, compound

Product 1

HCID 86593280HCID 86593280, compound

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of zinc chloride (2.79 g, 20.5 mmol) in diethyl ether (100 ml) was added sodium borohydride (1.55 g, 40.9 mmol), and the mixture was stirred at room temperature for 30 min. Insoluble material was filtered off, and to the filtrate was added a solution of ethyl 3-(4-fluorophenyl)-3-oxo-2-[(2,2,3,3-tetrafluoro-2,3-dihydro-1,4-benzodioxin-6-yl)methyl]propanoate (4.4 g, 10.2 mmol) in diethyl ether (50 ml) at 0° C. The mixture was stirred for 30 min. and 1N hydrochloric acid was added to stop the reaction. After neutralization with saturated aqueous sodium hydrogen carbonate solution, water (200 ml) was further 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 to give the objective substance (4.40 g, 100%).

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. customto give the objective substance (4.40 g, 100%)

Sources & evidence

ORD record
ord-a4370c64bb3d4da79c9681b8549ce480
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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