Potassium Carbonate → Ethyl-7-(1'-methoxycarbonyl-5-oxocyclopentyl)-heptanoate

HRID 2309557Notes

Reaction equation

HRID 2309557 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]Br)[CH3:2].C[C:14]1([C:20]([O-:22])=[O:21])[CH2:18][CH2:17][CH2:16][C:15]1=[O:19].[C:23](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]([O:3][C:4](=[O:12])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:14]1([C:20]([O:22][CH3:23])=[O:21])[C:15](=[O:19])[CH2:16][CH2:17][CH2:18]1)[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 122490Ethyl 7-bromoheptanoateHCID 18546588Methyl-2-oxocyclopentylcarboxylate

Product 1

HCID 13046296Ethyl-7-(1'-methoxycarbonyl-5-oxocyclopentyl)-heptanoateYield 12%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 10 g. of ethyl-7-bromoheptanoate and 5.9 g. of methyl-2-oxocyclopentylcarboxylate was refluxed for 20 hours in 100 ml. of dry acetone over 13 g. of anhydrous potassium carbonate in a nitrogen atmosphere. After cooling, the reaction mixture was filtered and the solvent removed at the rotovap. The residual oil was distilled on the Kugelrohr apparatus, with some unreacted bromoheptanoate first collected at 80° C., followed by distillation of product at 140° C. A total of 10.9 g. of product was obtained, with about 12-15% O-alkylated material.

Workup

  1. additionA mixture of 10 g
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture was filtered
  4. customthe solvent removed at the rotovap
  5. distillationThe residual oil was distilled on the Kugelrohr apparatus, with some unreacted bromoheptanoate
  6. customfirst collected at 80° C.
  7. distillationfollowed by distillation of product at 140° C

Sources & evidence

ORD record
ord-d22b19ea1bb84e318f7205890a8faf63
Source dataset
uspto-grants-1987_09
Patent number
US04695647

Reaction notes

Loading…