Water → HCID 57672310, compound

HRID 1645402Notes

Reaction equation

HRID 1645402 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=O)[C:5]2(O)[CH2:12][C:13](=[O:15])[CH3:14].C(OCC)(=O)C.O>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:12][CH:13]([OH:15])[CH3:14]

Participants

5

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 2728520HCID 2728520, compound

Product 1

HCID 57672310HCID 57672310, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The aldol product 48 (10 mmol) was dissolved in absolute THF (20 ml) under an Ar atmosphere. BH3xTHF (30 ml, 1 M solution, 30 mmol) was then added to the mixture, while cooling with a water bath, and the mixture was stirred at room temperature for 4 h. The course of the reaction was monitored by 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 ethyl acetate (30 ml each time). The combined organic phases were dried over Na2SO4 and concentrated under vacuo. 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 crystallizes spontaneously.

Workup

  1. temperaturewhile cooling with a water bath
  2. customAfter separation of the phases
  3. extractionthe aqueous phase was extracted twice with ethyl acetate (30 ml each time)
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. concentrationconcentrated under vacuo
  6. filtrationThe residue was filtered over silica gel with ethyl acetate
  7. customAfter removal of the solvent
  8. customthe product was obtained in the form of a sufficiently pure oil
  9. customcrystallizes spontaneously

Sources & evidence

ORD record
ord-13c6695acdbf4dbd880ebc8e3ddfd5af
Source dataset
uspto-grants-2012_02
Patent number
US08124788B2

Reaction notes

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