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Methyl 3-oxo-7,11,15-trimethylhexadeca-6,10,14-trienoate → [2-Hydroxy-6,10,14-trimethylpentadeca-5,9,13-trienyl]phosphonic acid

HRID 2379524
Notes
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Reaction equation

HRID 2379524 reaction equation
O=C(CCC=C(C)CCC=C(C)CCC=C(C)C)CC(OC)=O.[O:24]=[C:25]([CH2:33][CH2:34][CH:35]=[C:36]([CH3:48])[CH2:37][CH2:38][CH:39]=[C:40]([CH3:47])[CH2:41][CH2:42][CH:43]=[C:44]([CH3:46])[CH3:45])[CH2:26][P:27](=[O:32])([O:30]C)[O:28]C>>[OH:24][CH:25]([CH2:33][CH2:34][CH:35]=[C:36]([CH3:48])[CH2:37][CH2:38][CH:39]=[C:40]([CH3:47])[CH2:41][CH2:42][CH:43]=[C:44]([CH3:46])[CH3:45])[CH2:26][P:27](=[O:28])([OH:32])[OH:30]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 54245426Methyl 3-oxo-7,11,15-trimethylhexadeca-6,10,14-trienoateHCID 54462394Dimethyl [2-oxo-6,10,14-trimethylpentadeca-5,9,13-trienyl]phosphonate

Product 1

HCID 54248241[2-Hydroxy-6,10,14-trimethylpentadeca-5,9,13-trienyl]phosphonic acid

Procedure

This compound was prepared similarly by the method described in Step 2 of Example 1 except that methyl 3-oxo-7,11,15-trimethylhexadeca-6,10,14-trienoate was replaced by dimethyl [2-oxo-6,10,14-trimethyl-pentadeca-5,9,13-trienyl]phosphonate and the product from this reaction was used in the hydrolysis step similarly to the method used in Step 2 in Example 2 to give, after lyophilization, title compound as a nearly colorless gum.

Workup

  • customThis compound was prepared similarly by the method
  • customthe product from this reaction was used in the hydrolysis step similarly to the method
  • customto give
  • Sources & evidence

    ORD record
    ord-6bd5426d102d42cca2c0e0acaf3da6d3
    Source dataset
    uspto-grants-1994_11
    DOI
    10.6084/m9.figshare.5104873.v1
    Patent number
    US05362906

    Reaction notes

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    On this pageParticipantsProcedureWorkupSources & evidenceReaction notes