Water → 2-(5-fluoro-1H-indol-3-yl)ethanol

HRID 1645398Notes

Reaction equation

HRID 1645398 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]1(O)[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([F:15])[CH:13]=2)[NH:8][C:7]1=O)C.C(OCC)(=O)C.O>C1COCC1>[F:15][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:5][CH2:4][OH:3]

Participants

5

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 57475126HCID 57475126, compound

Product 1

HCID 136162482-(5-fluoro-1H-indol-3-yl)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The aldol product 34 (10 mmol) was dissolved in absolute THF (20 ml) under an argon atmosphere. BH3xTHF (40 ml, 1 M solution, 40 mmol) was then added to the mixture, and the mixture was stirred at room temperature for 14 hours. The course of the reaction was monitored of TLC. When the reaction had ended, the reaction solution was added to a mixture of ethyl acetate (50 ml) and H2O (50 ml). After separation of the phases, the aqueous phase was extracted twice with 30 ml portions of ethyl acetate. The combined organic phases were dried over Na2SO4 and concentrated under reduced pressure. The residue was filtered over silica gel with ethyl acetate. After removal of the solvent, the product was obtained in the form of a sufficiently pure oil and crystallized spontaneously.

Workup

  1. customAfter separation of the phases
  2. extractionthe aqueous phase was extracted twice with 30 ml portions of ethyl acetate
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. filtrationThe residue was filtered over silica gel with ethyl acetate
  6. customAfter removal of the solvent
  7. customthe product was obtained in the form of a sufficiently pure oil
  8. customcrystallized spontaneously

Sources & evidence

ORD record
ord-4b7766a68f05466fa820260fb4b129f2
Source dataset
uspto-grants-2012_02
Patent number
US08124788B2

Reaction notes

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