Hydrochloric Acid → HCID 90052452, compound

HRID 2284680Notes

Reaction equation

HRID 2284680 reaction equation
[F:1][C:2]([F:19])([CH:8]([F:18])[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=1)[C:3](OCC)=[O:4].[BH4-].[Na+].C(OCC)(=O)C.Cl>C(O)C>[F:1][C:2]([F:19])([CH:8]([F:18])[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=1)[CH2:3][OH:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 90052092HCID 90052092, compound

Product 1

HCID 90052452HCID 90052452, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 2,2,3-trifluoro-3-(3-nitrophenyl)propanoate (C30, 1.19 g) in ethanol (43 mL), sodium borohydride (811 mg) was added under ice cooling, and the mixture was stirred at room temperature for 40 minutes. To the reaction mixture, ethyl acetate and 1.0 mol/L aqueous hydrochloric acid were added. The organic layer was separated, washed successively with saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent, 100 to 40% hexane in ethyl acetate) to obtain 2,2,3-trifluoro-3-(3-nitrophenyl)propan-1-ol (C31, 829 mg).

Workup

  1. customThe organic layer was separated
  2. washwashed successively with saturated aqueous sodium hydrogencarbonate and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (eluent, 100 to 40% hexane in ethyl acetate)

Sources & evidence

ORD record
ord-2951aa6cd2104ecfa3011b28073d701e
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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