Cyclohexene → methyl (S)-8-hydroxy-4-[2-(3-pyridyloxy)ethyl]octanoate

HRID 465627Notes

Reaction equation

HRID 465627 reaction equation
C([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]([CH2:20][CH2:21][O:22][C:23]1[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=1)[CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])C1C=CC=CC=1.C1CCCCC=1>C(O)C.[OH-].[OH-].[Pd+2]>[OH:8][CH2:9][CH2:10][CH2:11][CH2:12][C@H:13]([CH2:20][CH2:21][O:22][C:23]1[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=1)[CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17]

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 10000174methyl (S)-8-(benzyloxy)-4-[2-(3-pyridyloxy)ethyl]octanoate

Product 1

HCID 9971741methyl (S)-8-hydroxy-4-[2-(3-pyridyloxy)ethyl]octanoate

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of methyl (S)-8-(benzyloxy)-4-[2-(3-pyridyloxy)ethyl]octanoate (1.1 g, 2.7 mmol) in ethanol (20 ml) is added cyclohexene (10.5 ml) followed by 20% palladium hydroxide on carbon (0.28 g). The mixture is heated at reflux for 18 hours. The catalyst is filtered off and washed with ethanol (3×10 ml). The solvent is evaporated and the residue purified by chromatography on silica gel using ethyl acetate as eluent to obtain methyl (S)-8-hydroxy-4-[2-(3-pyridyloxy)ethyl]octanoate; IR (CH2Cl2): 3600, 1732, 1282, 1230 cm-1.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 18 hours
  3. filtrationThe catalyst is filtered off
  4. washwashed with ethanol (3×10 ml)
  5. customThe solvent is evaporated
  6. customthe residue purified by chromatography on silica gel

Sources & evidence

ORD record
ord-f72e436307014d3dab484cb134afb9ed
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

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