HCID 68769595, compound → HCID 44129668, compound

HRID 448195Notes

Reaction equation

HRID 448195 reaction equation
[CH3:1][C:2]1[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[C:3]=1[C:4]([O:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13](=[O:26])[CH2:14][CH2:15][C:16]([O:18]CC2C=CC=CC=2)=[O:17])[CH:8]=1)=[O:5]>C(OCC)(=O)C.[Pd]>[CH3:31][C:27]1[CH:28]=[CH:29][CH:30]=[C:2]([CH3:1])[C:3]=1[C:4]([O:6][C:7]1[CH:8]=[C:9]([C:13](=[O:26])[CH2:14][CH2:15][C:16]([OH:18])=[O:17])[CH:10]=[CH:11][CH:12]=1)=[O:5]

Participants

4

Reactant 1

HCID 68769595HCID 68769595, compound

Product 1

HCID 44129668HCID 44129668, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 3-(4-(Benzyloxy)-4-oxobutanoyl)phenyl 2,6-dimethylbenzoate (Step C, 2.75 g, 6.6 mmol) in ethyl acetate was added Pd—C (5%, 0.230 g) under an argon atmosphere. The starting material was hydrogenated under a H2 atm for 14 hours and filtered through a celite pad. The filtrate was concentrated and purified by flash chromatography on a silica gel column (chloroform:methanol, 92.5:7.5 spiked with acetic acid) to provide the title compound.

Workup

  1. customwas hydrogenated under a H2 atm for 14 hours
  2. filtrationfiltered through a celite pad
  3. concentrationThe filtrate was concentrated
  4. custompurified by flash chromatography on a silica gel column (chloroform:methanol, 92.5:7.5 spiked with acetic acid)

Sources & evidence

ORD record
ord-20b73947ab224237ac6acd53c05b3297
Source dataset
uspto-grants-2013_07
Patent number
US08481595B2

Reaction notes

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