Hydrochloric Acid → HCID 22261567, compound

HRID 1610531Notes

Reaction equation

HRID 1610531 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:23]=[CH:22][C:21]([CH3:24])=[C:20]([O:25][C:26]([F:31])([F:30])[CH:27]([F:29])[F:28])[CH:19]=2)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][CH:5]=1.Cl.O>C(OCC)C.[Cl-].[Zn+2].[Cl-]>[F:3][C:4]1[CH:5]=[CH:6][C:7]([CH:10]([OH:32])[CH:11]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[C:20]([O:25][C:26]([F:31])([F:30])[CH:27]([F:29])[F:28])[CH:19]=2)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 22262321HCID 22262321, compound

Product 1

HCID 22261567HCID 22261567, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of zinc chloride (3.04 g, 22.3 mmol) in diethyl ether (70 ml) was added sodium borohydride (1.69 g, 44.6 mmol), and the mixture was stirred at room temperature for 30 min. Insoluble material was filtered off and a solution of ethyl 3-(4-fluorophenyl)-2-((4-methyl-3-((1,1,2,2-tetrafluoroethyl)oxy)phenyl)methyl)-3-oxopropionate (4.8 g, 11.2 mmol) in diethyl ether (50 ml) was added to the filtrate. The mixture was stirred at room temperature for 30 min. and 1N hydrochloric acid was added to the reaction solution under ice-cooling to quench 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 over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to give ethyl (2RS,3RS)-3-(4-fluorophenyl)-3-hydroxy-2-((4-methyl-3-((1,1,2,2-tetrafluoroethyl)oxy)phenyl)methyl)propionate (4.69 g, 97%) as a colorless oil.

Workup

  1. filtrationInsoluble material was filtered off
  2. stirringThe mixture was stirred at room temperature for 30 min.
  3. temperaturecooling
  4. customto quench
  5. customthe reaction
  6. extractionthe mixture was extracted with ethyl acetate (200 ml×2)
  7. washThe extract was washed with water and saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customevaporated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-990d2d22fed84b01bfffa6f894a81332
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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