Hydrochloric Acid → Benzyl 2(R)-benzyl-4-oxopentanoate

HRID 2380127Notes

Reaction equation

HRID 2380127 reaction equation
[CH2:1]([C@H:8]([CH2:19][CH:20]=[CH2:21])[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.CN(C)C=[O:26]>O.[Pd](Cl)Cl>[CH2:1]([C@H:8]([CH2:19][C:20](=[O:26])[CH3:21])[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 14989078Benzyl 2(S)-benzyl-4-pentenoate

Product 1

HCID 14989079Benzyl 2(R)-benzyl-4-oxopentanoateYield 86%

Reagents, catalysts & solvents 2

HCID 24290Palladium ChlorideCatalystHCID 962WaterSolvent

Procedure

A suspension of 500 mg (5 mmoles) of cuprous chloride and 180 mg (1 mmole) of palladium chloride in a mixture of 5 ml of dimethylformamide and 0.6 ml of water was stirred for 1 hour under an atmosphere of oxygen. At the end of this time, 1.41 g(5.03 mmoles) of benzyl 2(S)-benzyl-4-pentenoate (prepared as described in Preparation 18) was added to the mixture. The mixture was then stirred for an additional 5 hours at room temperature and under an atmosphere of oxygen, after which the reaction mixture was poured into 100 ml of 1N aqueous hydrochloric acid, and the mixture was extracted with methylene chloride. The extract was dried over anhydrous magnesium sulfate, the solvent was removed by distillation under reduced pressure, and the residue was purified by medium pressure silica gel column chromatography (using a 5:1 by volume mixture of hexane and ethyl acetate as eluent), to give 1.28 g (yield 86%) of the title compound as a colorless oily substance.

Workup

  1. stirringThe mixture was then stirred for an additional 5 hours at room temperature and under an atmosphere of oxygen
  2. extractionthe mixture was extracted with methylene chloride
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. customthe solvent was removed by distillation under reduced pressure
  5. customthe residue was purified by medium pressure silica gel column chromatography (
  6. additionby volume mixture of hexane and ethyl acetate as eluent),

Sources & evidence

ORD record
ord-ee08565e8a1942848c16b2407b2924f4
Source dataset
uspto-grants-1994_11
Patent number
US05364844

Reaction notes

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