Hydrochloric Acid → HCID 58020567, compound

HRID 1485073Notes

Reaction equation

HRID 1485073 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([CH:11]=[CH:12][C:13]=2[C:14]([F:17])([F:16])[F:15])[C:7](OC)=[O:8])[CH2:3][CH2:2]1.[BH4-].[Li+].Cl>O1CCCC1>[CH:1]1([C:4]2[CH:5]=[C:6]([CH2:7][OH:8])[CH:11]=[CH:12][C:13]=2[C:14]([F:16])([F:17])[F:15])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4148881Lithium borohydrideHCID 58020608HCID 58020608, compound

Product 1

HCID 58020567HCID 58020567, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution in dehydrated tetrahydrofuran (50.0 mL) of the compound (1.42 g) obtained in step (1) above, lithium borohydride (380 mg) was added and the mixture was stirred at 60° C. for 4 hours. Subsequently, 1 mol/L hydrochloric acid was added under cooling with ice. Following extraction with ethyl acetate, the organic layer was washed with saturated brine. After drying over anhydrous magnesium sulfate and removing the desiccant by filtration, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=98:2-75:25) to give [3-cyclopropyl-4-(trifluoromethyl)phenyl]methanol as a colorless oil (1.18 g).

Workup

  1. temperatureunder cooling with ice
  2. extractionextraction with ethyl acetate
  3. washthe organic layer was washed with saturated brine
  4. dry with materialAfter drying over anhydrous magnesium sulfate
  5. customremoving the
  6. filtrationdesiccant by filtration
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=98:2-75:25)

Sources & evidence

ORD record
ord-350a45a36d1b4503b199557c60ed2c60
Source dataset
uspto-grants-2016_08
Patent number
US09422240B2

Reaction notes

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