Ethyl acetate hexane → HCID 86612734, compound

HRID 1821547Notes

Reaction equation

HRID 1821547 reaction equation
C([O:8][C@H:9]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C@@H:17]([OH:20])[CH2:18][CH3:19])[CH3:10])C1C=CC=CC=1.C(OCC)(=O)C.CCCCCC>C(O)C.[Pd]>[CH3:10][C@H:9]([OH:8])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C@@H:17]([OH:20])[CH2:18][CH3:19]

Participants

5

Reactant 2

HCID 21226206Ethyl acetate hexaneHCID 69050013HCID 69050013, compound

Product 1

HCID 86612734HCID 86612734, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1.95 g (7 mmol) (2S,9S)-2-benzyloxyundecane-9-ol in 30 ml ethanol was added 20 mg Pd/C-catalyst. Hydrogenation was carried out over a period of 12 h at a pressure of 40 atm. After completion of the reaction, the catalyst was filtered off over silica, and the solution was concentrated in vacuo. Flash chromatography (ethyl acetate:hexane 1:1) yielded 1.2 g (6.4 mmol, 92%) (2S,9S)-undecane-2,9-diol.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe catalyst was filtered off over silica
  3. concentrationthe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-755455fa5dde4fb89a80b17227a21b24
Source dataset
uspto-grants-2009_10
Patent number
US07608254B2

Reaction notes

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