Benzyl 2(R)-benzyl-4-oxopentanoate → 2(R)-benzyl-4-oxopentanoic acid

HRID 2380128Notes

Reaction equation

HRID 2380128 reaction equation
[CH2:1]([C@H:8]([CH2:19][C:20](=[O:22])[CH3:21])[C:9]([O:11]CC1C=CC=CC=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>C(O)C.[Pd]>[CH2:1]([C@H:8]([CH2:19][C:20](=[O:22])[CH3:21])[C:9]([OH:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14989079Benzyl 2(R)-benzyl-4-oxopentanoateHCID 178418361HCID 178418361, compound

Product 1

HCID 149890802(R)-benzyl-4-oxopentanoic acidYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution or 1.00 g (3.37 mmoles) of benzyl 2(R)-benzyl-4-oxopentanoate (prepared as described in Preparation 19) in 10 ml of ethanol was stirred at room temperature for 3 hours in the presence of 100 mg of 10% w/w palladium-on-charcoal and under about 4 atmospheres of hydrogen. At the end of this time, the catalyst was removed by filtration, and then the solvent was removed by distillation under reduced pressure. The residue was recrystallized from a mixture of hexane and diisopropyl ether, to give 610 mg (yield 88%) of the title compound as white crystals, melting at 71°-73° C.

Workup

  1. customAt the end of this time, the catalyst was removed by filtration
  2. customthe solvent was removed by distillation under reduced pressure
  3. customThe residue was recrystallized from a mixture of hexane and diisopropyl ether

Sources & evidence

ORD record
ord-f6c5a2c727354d6589838e841fd98a15
Source dataset
uspto-grants-1994_11
Patent number
US05364844

Reaction notes

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