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

HRID 2309555Notes

Reaction equation

HRID 2309555 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].[CH2:13]([O:20][C:21]([CH:23]1[CH2:27][CH2:26][CH2:25][C:24]1=[O:28])=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=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:23]1([C:21]([O:20][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[O:22])[C:24](=[O:28])[CH2:25][CH2:26][CH2:27]1)[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 122490Ethyl 7-bromoheptanoateHCID 9794427Benzyl 2-oxocyclopentane-1-carboxylate

Product 1

HCID 13935329Ethyl-7-(1'-benzyloxycarbonyl-5'-oxocyclopentyl)-heptanoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a 100 ml. RB flask was added 13 g. to Ethyl-7-bromoheptanoate and 12.8 g. of 2-benzyloxycarbonylcyclopentanone. The reactants were dissolved in 50 ml. of anhydrous acetone and refluxed over 17 g. of anhydrous potassium carbonate under nitrogen for 20 hours. The reaction mixture was then cooled and filtered and the filtrate evaporated to afford 22.1 g. of crude oil, which was not further purified at this stage.

Workup

  1. additionRB flask was added 13 g
  2. dissolutionThe reactants were dissolved in 50 ml
  3. temperatureThe reaction mixture was then cooled
  4. filtrationfiltered
  5. customthe filtrate evaporated
  6. customto afford 22.1 g
  7. customof crude oil, which was not further purified at this stage

Sources & evidence

ORD record
ord-6cfdabc3aa94465bbe862e228bdf732c
Source dataset
uspto-grants-1987_09
Patent number
US04695647

Reaction notes

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