Ethyl 3-bromopropionate → HCID 22343049, compound

HRID 584128Notes

Reaction equation

HRID 584128 reaction equation
[O-]CC.[Na+].[C:5]1([CH3:16])[CH:10]=[CH:9][C:8]([C:11]2[NH:15][N:14]=[N:13][N:12]=2)=[CH:7][CH:6]=1.Br[CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]>C(O)C>[CH2:23]([O:22][C:20](=[O:21])[CH2:19][CH2:18][N:13]1[N:14]=[N:15][C:11]([C:8]2[CH:7]=[CH:6][C:5]([CH3:16])=[CH:10][CH:9]=2)=[N:12]1)[CH3:24]

Participants

5

Reactant 3

HCID 68320Ethyl 3-bromopropionateHCID 2723922Sodium ethoxideHCID 178424083HCID 178424083, compound

Product 1

HCID 22343049HCID 22343049, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium ethoxide (21%, 173 μL, 0.536 mmol) was dissolved in 650 μL absolute ethanol along with 5-p-tolyl tetrazole (65.9 mmol) at reflux. Ethyl 3-bromo-propionate (69 μL, 0.536 mmol) was added at reflux and the mixture was maintained at reflux overnight. The crude mixtures were filtered, concentrated and extracted with diethyl ether and sat. NaHCO3. The organic layers were dried and evaporated. When necessary, further purification was performed by RP-HPLC to provide ethyl-3-(5-p-tolyl-2-tetrazolyl)propionate.

Workup

  1. temperatureat reflux
  2. temperatureat reflux
  3. temperaturethe mixture was maintained
  4. temperatureat reflux overnight
  5. filtrationThe crude mixtures were filtered
  6. concentrationconcentrated
  7. extractionextracted with diethyl ether and sat. NaHCO3
  8. customThe organic layers were dried
  9. customevaporated
  10. customWhen necessary, further purification

Sources & evidence

ORD record
ord-21b2eadddd8645418a57c6164dd89393
Source dataset
uspto-grants-2005_08
Patent number
US06924284B2

Reaction notes

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