Acetic Acid → ethyl (6E)-6-[(4-hydroxyphenyl)methoxyimino]-6-phenylhexanoate

HRID 2299752Notes

Reaction equation

HRID 2299752 reaction equation
[Si]([O:8][C:9]1[CH:17]=[CH:16][C:12]([CH2:13][O:14][NH2:15])=[CH:11][CH:10]=1)(C(C)(C)C)(C)C.O=[C:19]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25].C(O)(=O)C.C([O-])(=O)C.[Na+]>C(OCC)(=O)C.CCCCCC.O.C(O)C>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][O:14]/[N:15]=[C:19](/[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)\[CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:16][CH:17]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 517045Sodium AcetateHCID 3681727Ethyl 6-oxo-6-phenylhexanoateHCID 118211174-(Tert-butyldimethylsilyloxy)benzyloxyamine

Product 1

HCID 11089565ethyl (6E)-6-[(4-hydroxyphenyl)methoxyimino]-6-phenylhexanoateYield 77%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

A mixture of 4-(tert-butyldimethylsilyloxy)benzyloxyamine (5.31 g), ethyl 6-oxo-6-phenylhexanoate (6.76 g), acetic acid (3.54 ml), sodium acetate (3.38 g) and ethanol (150 ml) was heated to reflux for 18 hours. The reaction mixture was cooled to room temperature, water was added and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The residue was dissolved in tetrahydrofuran (100 ml), tetrabutylammonium fluoride trihydrate (10.0 g) was added and stirred at room temperature for 1 hour. Water was added to the reaction mixture and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The residue was subjected to silica gel chromatography to obtain ethyl E-6-(4-hydroxybenzyloxyimino)-6-phenylhexanoate (5.64 g, yield 77%) as a colorless oil from an ethyl acetate-hexane (2:7, v/v)-eluted fraction.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 18 hours
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in tetrahydrofuran (100 ml)
  8. additiontetrabutylammonium fluoride trihydrate (10.0 g) was added
  9. additionWater was added to the reaction mixture
  10. extractionextracted with ethyl acetate
  11. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  12. dry with materialdried (MgSO4)
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-b0fc1d83be9c4805aa910dde2f4ad779
Source dataset
uspto-grants-2002_12
Patent number
US06495581B1

Reaction notes

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