Ethyl bromoacetate → HCID 12132633, compound

HRID 393252Notes

Reaction equation

HRID 393252 reaction equation
[C:1]([CH:3]1[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH2:10][C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)#[N:2].[O-]CC.[Na+].Br[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]>CCO>[CH2:26]([O:25][C:23](=[O:24])[CH2:22][C:3]1([C:1]#[N:2])[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:9]=2[CH2:10][C:11]2[C:16]1=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:27]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 2723922Sodium ethoxideHCID 10536730HCID 10536730, compound

Product 1

HCID 12132633HCID 12132633, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

9-Cyano-9,10-dihydroanthracene [2] (1.25 g, 6.09 mmol) was added to sodium ethoxide prepared from Na (0.196 g, 8.53 mmol) and EtOH (10 mL) and heated at reflux (1 hr). The solution was then cooled in an ice bath and ethyl bromoacetate (1.42 g, 8.53 mmol) was added drop wise via a syringe. The resulting mixture was heated at reflux (4 h) cooled and filtered. The residue was washed with ether (25 mL). Water (25 mL) was added to the filterate and the organic layer was separated. The aqueous layer was once again extracted with ether (25 mL). The combined ether extracts were washed with water and brine, dried (MgSO4) and evaporated under reduced pressure to give an oil which was purified by mplc using pet. ether: EtOAc (9:1) as eluent to give 1.245 g (70%) of the product as a colorless oil, which crystallized on prolonged standing: mp 69-70° C. (EtOAc-pet. ether). 1H NMR (CDCl3)d: 1.10-1.15 (t, J=7.5 Hz, CH3), 2.85 (s, 2H, CH2), 3.97-4.14 (m, 4H, CH2), 7.33-7.89 (m, 8H, Ar—H). 13C NMR (CDCl3)d: 14.53, 35.27, 46.05, 46.28, 61.63, 121.89, 127.58, 127.70, 128.93, 134.21, 135.10, 167.96

Workup

  1. temperatureheated
  2. temperatureat reflux (1 hr)
  3. temperatureThe solution was then cooled in an ice bath
  4. temperatureThe resulting mixture was heated
  5. temperatureat reflux (4 h)
  6. temperaturecooled
  7. filtrationfiltered
  8. washThe residue was washed with ether (25 mL)
  9. additionWater (25 mL) was added to the filterate
  10. customthe organic layer was separated
  11. extractionThe aqueous layer was once again extracted with ether (25 mL)
  12. washThe combined ether extracts were washed with water and brine
  13. dry with materialdried (MgSO4)
  14. customevaporated under reduced pressure
  15. customto give an oil which
  16. customwas purified by mplc

Sources & evidence

ORD record
ord-3759e83cbf63450d992a6f2eb0feec51
Source dataset
uspto-grants-2004_10
Patent number
US06806283B2

Reaction notes

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