Ethyl-7-(1'-benzyloxycarbonyl-5'-oxocyclopentyl)-heptanoate → Ethyl 7-(2-oxocyclopentyl)heptanoate

HRID 2309556Notes

Reaction equation

HRID 2309556 reaction equation
[CH2:1]([O:3][C:4](=[O:27])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1(C(OCC2C=CC=CC=2)=O)[C:15](=[O:16])[CH2:14][CH2:13][CH2:12]1)[CH3:2].[H][H]>[Pd].C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:27])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH:11]1[CH2:12][CH2:13][CH2:14][C:15]1=[O:16])[CH3:2]

Participants

5

Reactant 2

HCID 13935329Ethyl-7-(1'-benzyloxycarbonyl-5'-oxocyclopentyl)-heptanoateHCID 178418361HCID 178418361, compound

Product 1

HCID 558615Ethyl 7-(2-oxocyclopentyl)heptanoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
130 °C

Procedure

The crude oil from (ii) above was dissolved in 50 ml. of toluene and reduced over 1 g. of 5% Pd on carbon under 50 psi of hydrogen for 20 hours. The catalyst was removed by filtration and the filtrate refluxed two hours to complete decarboxylation. The toluene was subsequently removed by evaporation and the residual oil distilled on the Kugelrohr apparatus. Heating to 130° C. removed the volatile impurities, and the bulk of the desired product was collected at 175°-180° C. Yield was 11.2 g. (79%).

Workup

  1. customThe catalyst was removed by filtration
  2. temperaturethe filtrate refluxed two hours
  3. customThe toluene was subsequently removed by evaporation
  4. distillationthe residual oil distilled on the Kugelrohr apparatus
  5. customremoved the volatile impurities
  6. customthe bulk of the desired product was collected at 175°-180° C

Sources & evidence

ORD record
ord-393d0635b16f4064b7a962e8d432ab6d
Source dataset
uspto-grants-1987_09
Patent number
US04695647

Reaction notes

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