Ethyl 3-bromopropionate → HCID 20491693, compound

HRID 1154030Notes

Reaction equation

HRID 1154030 reaction equation
[Na].[O:2]=[C:3]1[N:7]2[CH2:8][CH2:9][CH2:10][CH:11]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[N:6]2[C:5](=[O:19])[CH2:4]1.Br[CH2:21][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]>C(O)C>[CH2:26]([O:25][C:23]([CH2:22][CH2:21][C:4]1([CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:3](=[O:2])[N:7]2[CH2:8][CH2:9][CH2:10][CH:11]([C:12]([O:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[O:13])[N:6]2[C:5]1=[O:19])=[O:24])[CH3:27]

Participants

5

Reactant 3

HCID 68320Ethyl 3-bromopropionateHCID 5360545SodiumHCID 13774859HCID 13774859, compound

Product 1

HCID 20491693HCID 20491693, compoundYield 18.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

(b) 0.43 g of sodium was dissolved in 20 ml of ethanol. A solution of 2.27 g of tert.butyl hexahydro-1,3-dioxo-1H-pyrazolo[1,2-a]pyridazine-5-carboxylate in 20 ml of ethanol was added and the mixture was heated under reflux for 2 hours. 5 g of ethyl 3-bromopropionate were added and the mixture was heated under reflux for an additional 2 hours. The solvent was removed and the residue was partitioned between dichloromethane and 2N hydrochloric acid. The organic layer was separated and evaporated. The residue was chromatographed on silica gel to give 0.37 g (9%) of tert.butyl 2,2-bis(2-ethoxycarbonylethyl)-hexahydro-1,3-dioxo-1H-pyrazolo[1,2-a]pyridazine-5-carboxylate in the form of an oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for an additional 2 hours
  5. customThe solvent was removed
  6. customthe residue was partitioned between dichloromethane and 2N hydrochloric acid
  7. customThe organic layer was separated
  8. customevaporated
  9. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-669e88fc5ffc4fa696f320aeb0e62563
Source dataset
uspto-grants-1984_12
Patent number
US04487929

Reaction notes

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