Bromocyclopentane → Ethyl 2-cyclopentyl-3-oxobutanoate

HRID 1986635Notes

Reaction equation

HRID 1986635 reaction equation
[O:1]=[C:2]([CH3:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH:10]1(Br)[CH2:14][CH2:13][CH2:12][CH2:11]1.[O-]CC.[Na+]>C(O)C>[CH:10]1([CH:3]([C:2](=[O:1])[CH3:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 8728BromocyclopentaneHCID 8868Ethyl AcetoacetateHCID 2723922Sodium ethoxide

Product 1

HCID 17750296Ethyl 2-cyclopentyl-3-oxobutanoateYield 71.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
22.5 °C

Procedure

A mixture of ethyl 3-oxobutanoate (0.5 mol), cyclopentyl bromide (0.5 mol) and sodium ethoxide (0.5 mol) in ethanol (100 ml) was heated under reflux for 15 hours. The reaction mixture was cooled to about 20-25° C., and 71 g of the title compound were then isolated by distillation (96-100° C., 0.25 mbar).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 15 hours

Sources & evidence

ORD record
ord-8c73c4e6b5464a378dd33382e6940fab
Source dataset
uspto-grants-2009_06
Patent number
US07550471B2

Reaction notes

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