Methyl (7E)-8-{2-[(4-cyclohexylbenzyl)oxy]phenyl}-6-oxo-7-octenoate → Methyl 8-{2-[(4-cyclohexylbenzyl)oxy]phenyl}-6-oxooctanoate

HRID 2243295Notes

Reaction equation

HRID 2243295 reaction equation
[CH:1]1([C:7]2[CH:32]=[CH:31][C:10]([CH2:11][O:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3/[CH:19]=[CH:20]/[C:21](=[O:30])[CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>C(OCC)(=O)C.[Pd]>[CH:1]1([C:7]2[CH:32]=[CH:31][C:10]([CH2:11][O:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[CH2:19][CH2:20][C:21](=[O:30])[CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27])=[CH:9][CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 1

HCID 59210853Methyl (7E)-8-{2-[(4-cyclohexylbenzyl)oxy]phenyl}-6-oxo-7-octenoate

Product 1

HCID 59210668Methyl 8-{2-[(4-cyclohexylbenzyl)oxy]phenyl}-6-oxooctanoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 2.80 g (6.44 mmol) of methyl (7E)-8-{2-[(4-cyclohexylbenzyl)-oxy]phenyl}-6-oxo-7-octenoate XIII and 0.06 g of Pd/C (10% Pd) in 30 ml of ethyl acetate was stirred under an atmosphere of hydrogen for 3 h. The catalyst was removed by filtration through Celite, and the product was purified chromatographically (silica gel, cyclohexane/ethyl acetate 20:1).

Workup

  1. customThe catalyst was removed by filtration through Celite
  2. customthe product was purified chromatographically (silica gel, cyclohexane/ethyl acetate 20:1)

Sources & evidence

ORD record
ord-43abae2605a64014a979ea4f6756e320
Source dataset
uspto-grants-2010_03
Patent number
US07674825B2

Reaction notes

Loading…