Water → HCID 12541369, compound

HRID 1109103Notes

Reaction equation

HRID 1109103 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][C:7](=[O:13])[CH2:8]2.N1CCCC1.O.Br[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][C:7](=[O:13])[CH:8]2[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 31268PyrrolidineHCID 2591945-Methoxy-2-tetralone

Product 1

HCID 12541369HCID 12541369, compoundYield 43.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

28 g (0.16 mol) of 5-methoxy-2-tetralone and 12.5 g (14.5 ml, 0.175 mol) of pyrrolidine were dissolved in 150 ml of toluene. The mixture was boiled on a water separator for 2 hours, cooled, treated with 31.7 g (0.19 mol) of ethyl bromoacetate and boiled under reflux for 2 hours. The mixture was then concentrated, dissolved in 150 ml of ethanol/water (5:1) and again boiled under reflux for 2 hours. The solvent was distilled off in a vacuum and the residue was dissolved in ethyl acetate. The solution was washed with water and saturated sodium chloride solution, dried with MgSO4, filtered and concentrated. The residue was dissolved in ether, treated with active charcoal and recrystallized. There were obtained 18.4 g of ethyl rac-1,2,3,4-tetrahydro-5-methoxy-2-oxo-1-napthylacetate as white crystals. A further 10.3 g of white crystals could be obtained from the mother liquors by chromatography over silica gel with cyclohexane/ethyl acetate (4:1). Total yield: 28.7 g (68%) of white crystals with m.p. 36°-40°.

Workup

  1. temperaturecooled
  2. temperatureunder reflux for 2 hours
  3. concentrationThe mixture was then concentrated
  4. dissolutiondissolved in 150 ml of ethanol/water (5:1)
  5. temperatureunder reflux for 2 hours
  6. distillationThe solvent was distilled off in a vacuum
  7. dissolutionthe residue was dissolved in ethyl acetate
  8. washThe solution was washed with water and saturated sodium chloride solution
  9. dry with materialdried with MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. dissolutionThe residue was dissolved in ether
  13. additiontreated with active charcoal
  14. customrecrystallized

Sources & evidence

ORD record
ord-976fa6435fe34254858bb6bac0bd9ab1
Source dataset
uspto-grants-1994_06
Patent number
US05318966

Reaction notes

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