Water → HCID 13271018, compound

HRID 1645400Notes

Reaction equation

HRID 1645400 reaction equation
O[C:2]1([CH2:13][C:14](=[O:16])[CH3:15])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH3:11])[CH:9]=2)[NH:4][C:3]1=O.C(OCC)(=O)C.O>C1COCC1>[CH3:11][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[NH:4][CH:3]=[C:2]2[CH2:13][CH:14]([OH:16])[CH3:15]

Participants

5

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 2887745HCID 2887745, compound

Product 1

HCID 13271018HCID 13271018, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The aldol product 47 (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 15 hours. 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 30 ml portions of ethyl acetate. The combined organic phases were dried over Na2SO4 and concentrated in vacuo. The residue was filtered over silica gel with ethyl acetate. The crude product obtained after removal of the solvent was purified by column chromatography on silica gel (eluent:ethyl acetate/cyclohexane: 1:2).

Workup

  1. temperaturewhile cooling with a water bath
  2. customAfter separation of the phases
  3. extractionthe aqueous phase was extracted twice with 30 ml portions of ethyl acetate
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. filtrationThe residue was filtered over silica gel with ethyl acetate

Sources & evidence

ORD record
ord-84c3688a8e184dc98b0efcdcd4745cdd
Source dataset
uspto-grants-2012_02
Patent number
US08124788B2

Reaction notes

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