Hydrochloric Acid → ethyl (2RS,3RS)-3-(4-fluorophenyl)-3-hydroxy-2-((5-(trifluoromethyl)-2-furanyl)methyl)propionate

HRID 1610330Notes

Reaction equation

HRID 1610330 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:27])[CH:11]([CH2:17][C:18]2[O:19][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:21][CH:22]=2)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][CH:5]=1.Cl>C(OCC)C.[Cl-].[Zn+2].[Cl-]>[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([OH:27])[CH:11]([CH2:17][C:18]2[O:19][C:20]([C:23]([F:24])([F:25])[F:26])=[CH:21][CH:22]=2)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 22261966Ethyl 3-(4-fluorophenyl)-3-oxo-2-((5-(trifluoromethyl)-2-furanyl)methyl)propionate

Product 1

HCID 86593231ethyl (2RS,3RS)-3-(4-fluorophenyl)-3-hydroxy-2-((5-(trifluoromethyl)-2-furanyl)methyl)propionateYield 78.1%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of zinc chloride (3.35 g, 24.6 mmol) in diethyl ether (70 ml) was added sodium borohydride (1.86 g, 49.1 mmol) and the mixture was stirred at room temperature for 30 min. The insoluble material was filtered off. To the filtrate was added a solution of ethyl 3-(4-fluorophenyl)-3-oxo-2-((5-(trifluoromethyl)-2-furanyl)methyl)propionate (4.40 g, 12.3 mmol) in diethyl ether (30 ml) and the mixture was stirred at room temperature for 2 hrs. 1N Hydrochloric acid was added to the reaction solution under ice-cooling for quenching, water (100 ml) was further added, and the mixture as extracted with ethyl acetate (100 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-((5-(trifluoromethyl)-2-furanyl)methyl)propionate (3.46 g, 78%).

Workup

  1. filtrationThe insoluble material was filtered off
  2. stirringthe mixture was stirred at room temperature for 2 hrs
  3. temperaturecooling
  4. customfor quenching
  5. additionwater (100 ml) was further added
  6. extractionthe mixture as extracted with ethyl acetate (100 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-0af3491a7ac840308c535f4b07ea0812
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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