(3Z)-(5S)-5,9-Dimethyl-dec-3-ene-1,9-diol → (R)-5,9-dimethyl-decane-1,9-diol

HRID 493068Notes

Reaction equation

HRID 493068 reaction equation
[CH3:1][C@@H:2]([CH2:8][CH2:9][CH2:10][C:11]([CH3:14])([OH:13])[CH3:12])/[CH:3]=[CH:4]\[CH2:5][CH2:6][OH:7].[H][H]>C(OCC)(=O)C.[Pd]>[CH3:1][C@@H:2]([CH2:8][CH2:9][CH2:10][C:11]([CH3:14])([OH:13])[CH3:12])[CH2:3][CH2:4][CH2:5][CH2:6][OH:7]

Participants

5

Reactant 2

HCID 57680494(3Z)-(5S)-5,9-Dimethyl-dec-3-ene-1,9-diolHCID 178418361HCID 178418361, compound

Product 1

HCID 15859989(R)-5,9-dimethyl-decane-1,9-diolYield 100.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of diol 13 (55 mg, 0.27 mmol) in ethyl acetate (10 mL) was added Pd/C (10%, 50 mg). The reaction mixture was stirred for 18 hours under a continuous stream of hydrogen at room temperature. The mixture was then filtered, and the solvent was evaporated under reduced pressure. The crude oily product was chromatographed on silica Sep-Pak cartridge eluted with hexane/EtOAc (8:2) to give an oily diol 14 (55 mg, 45%).

Workup

  1. filtrationThe mixture was then filtered
  2. customthe solvent was evaporated under reduced pressure
  3. customThe crude oily product was chromatographed on silica Sep-Pak cartridge
  4. washeluted with hexane/EtOAc (8:2)

Sources & evidence

ORD record
ord-3f4ed69f44ae41e8a173d4075ec1f021
Source dataset
uspto-grants-2009_05
Patent number
US07534777B2

Reaction notes

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